Triethylamine → 2-amino-5-(2-(dimethylamino)ethoxy)-N-(4-methylpyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 869127Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 869127
[NH2:1][C:2]1[C:16]([C:17]([OH:19])=O)=[C:5]2[N:6]=[C:7]([O:10][CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])[CH:8]=[CH:9][N:4]2[N:3]=1.CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:49][C:50]1[CH:55]=[CH:54][N:53]=[CH:52][C:51]=1[NH2:56]>CN1C(=O)CCC1>[NH2:1][C:2]1[C:16]([C:17]([NH:56][C:51]2[CH:52]=[N:53][CH:54]=[CH:55][C:50]=2[CH3:49])=[O:19])=[C:5]2[N:6]=[C:7]([O:10][CH2:11][CH2:12][N:13]([CH3:14])[CH3:15])[CH:8]=[CH:9][N:4]2[N:3]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 1379353-Amino-4-picolineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 904115212-Amino-5-(2-(dimethylamino)ethoxy)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

Produkt 1

HCID 904186462-amino-5-(2-(dimethylamino)ethoxy)-N-(4-methylpyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamideAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a suspension of 2-amino-5-[2-(dimethylamino)ethoxy]pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (100 mg, 0.377 mmol) in NMP (667 μL) was added Et3N (46.54 mg, 64.1 μL, 0.4599 mmol) in one portion. The mixture was stirred for 10 minutes before adding TBTU (Boron Tetrafluoride Ion) (136.3 mg, 0.4245 mmol), portionwise, over 5 minutes. The mixture was allowed to stir at room temperature for 20 mins. 4-Methylpyridin-3-amine (40.77 mg, 0.377 mmol) was added and the mixture was heated to 100° C. for 4 hours. The mixture was filtered through a silica gel pad and eluted with DCM initially followed by 20/80 MeOH/DCM. The residue was further purified by preparative HPLC to provide compound I-C-3 (42% yield). LC-MS (M+H)+=356.2; 1H NMR (500 MHz, DMSO-d6) δ 9.80 (s, 1H), 9.38 (brs, 1H), 9.20 (brs, 1H), 8.82 (d, 1H), 8.50-8.43 (m, 1H), 7.66-7.6 (m, 1H), 6.62 (d, 1H), 6.50 (brs, 2H), 4.81-4.78 (m, 2H), 3.63-3.60 (m, 2H), 2.95 (s, 6H), 2.55 (s, 3H);

Aufarbeitung

  1. waitportionwise, over 5 minutes
  2. stirringto stir at room temperature for 20 mins
  3. filtrationThe mixture was filtered through a silica gel pad
  4. washeluted with DCM
  5. customThe residue was further purified by preparative HPLC
  6. customto provide compound I-C-3 (42% yield)

Quellen und Nachweise

ORD-Eintrag
ord-591961557a044b8e81996aaf7472d4b3
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969360B2

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