7-Chloropyrazolo[1,5-a]pyrimidin-5-amine → HCID 86652262, Verbindung

HRID 1409122

Reaktionsgleichung

Reaktionsgleichung von HRID 1409122
[Cl:1][C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([NH2:11])[CH:3]=1.[Cl:12][C:13]1[N:18]2[N:19]=[C:20]([CH3:22])[CH:21]=[C:17]2[N:16]=[C:15]([NH2:23])[CH:14]=1.[Cl:24][C:25]1[N:30]2[N:31]=[C:32]([CH2:34][CH3:35])[CH:33]=[C:29]2[N:28]=[C:27]([NH2:36])[CH:26]=1.[Cl:37][C:38]1[N:43]2[N:44]=[C:45]([CH:47]3[CH2:49][CH2:48]3)[CH:46]=[C:42]2[N:41]=[C:40]([NH2:50])[CH:39]=1.[Cl-].[CH3:52][O:53][C:54](=[O:64])[C:55]1[CH:63]=[CH:62][C:58]([C:59]([OH:61])=[O:60])=[CH:57][CH:56]=1>N1C=CC=CC=1>[Cl:1][C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([NH:11][C:59]([C:58]2[CH:62]=[CH:63][C:55]([C:54]([O:53][CH3:52])=[O:64])=[CH:56][CH:57]=2)=[O:60])[CH:3]=1.[Cl:12][C:13]1[N:18]2[N:19]=[C:20]([CH3:22])[CH:21]=[C:17]2[N:16]=[C:15]([NH:23][C:59]([C:58]2[CH:57]=[CH:56][C:55]([C:54]([O:53][CH3:52])=[O:64])=[CH:63][CH:62]=2)=[O:61])[CH:14]=1.[Cl:24][C:25]1[N:30]2[N:31]=[C:32]([CH2:34][CH3:35])[CH:33]=[C:29]2[N:28]=[C:27]([NH:36][C:59]([C:58]2[CH:62]=[CH:63][C:55]([C:54]([O:53][CH3:52])=[O:64])=[CH:56][CH:57]=2)=[O:60])[CH:26]=1.[Cl:37][C:38]1[N:43]2[N:44]=[C:45]([CH:47]3[CH2:48][CH2:49]3)[CH:46]=[C:42]2[N:41]=[C:40]([NH:50][C:59]([C:58]2[CH:62]=[CH:63][C:55]([C:54]([O:53][CH3:52])=[O:64])=[CH:56][CH:57]=2)=[O:60])[CH:39]=1

Komponenten

10

Edukt 5

HCID 442513067-Chloropyrazolo[1,5-a]pyrimidin-5-amineHCID 442513077-Chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-amineHCID 442513087-Chloro-2-ethylpyrazolo[1,5-a]pyrimidin-5-amineHCID 44251312HCID 44251312, VerbindungHCID 53442854Terephthalic acid monomethylester chloride

Produkt 4

HCID 86652259Methyl 4-(7-chloropyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)benzoateAusbeute 92 %HCID 86652260Methyl 4-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)benzoateAusbeute 72 %HCID 86652261Methyl 4-(7-chloro-2-ethylpyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)benzoateAusbeute 84 %HCID 86652262HCID 86652262, VerbindungAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

7-Chloropyrazolo[1,5-a]pyrimidin-5-amine (1E, 1.0 equivalent), 7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-amine (1J, 1.0 equivalent), 7-chloro-2-ethylpyrazolo[1,5-a]pyrimidin-5-amine (1O, 1.0 equivalent), or 7-chloro-2-cyclopropylpyrazolo[1,5-a]pyrimidin-5-amine (1S, 1.0 equivalent) was suspended in pyridine (0.3 M). At 0° C. was added terephthalic acid monomethylester chloride (2B, 1.3 equivalents), and the mixture was stirred vigorously at 0° C. for 4-18 h. The reaction was quenched with saturated NaHCO3 and stirred for another 0.5 h; pyridine was removed in vacuo and the residue was suspended in water. The precipitate was collected on a fritted glass funnel and was washed twice with water. After drying under a stream of N2 for 15 h, the crude product methyl 4-(7-chloropyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)benzoate 2C (92%), methyl 4-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)benzoate 2E (72%), methyl 4-(7-chloro-2-ethylpyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)benzoate 2G (84%) or methyl 4-(7-chloro-2-cyclopropylpyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)benzoate 2I (98%) was obtained as an orange solid and was used without further purification.

Aufarbeitung

  1. customThe reaction was quenched with saturated NaHCO3
  2. stirringstirred for another 0.5 h
  3. custompyridine was removed in vacuo
  4. customThe precipitate was collected on a fritted glass funnel
  5. washwas washed twice with water
  6. dry with materialAfter drying under a stream of N2 for 15 h

Quellen und Nachweise

ORD-Eintrag
ord-53a357503d2a448d8761ad4e1d76117f
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921358B2

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