Acetic Acid → (S)-tert-butyl 4-(2-(3-((4-(diethylamino)-2-(4-((1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl) pyridin-2-yl)phenyl)carbamoyl)-N-methylbenzamido)ethyl)-1,4-diazepane-1-carboxylate

HRID 1408206Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1408206
[CH2:1]([N:3]([CH2:45][CH3:46])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:25])[C:12]2[CH:24]=[CH:23][CH:22]=[C:14]([C:15]([N:17]([CH3:21])[CH2:18][CH:19]=O)=[O:16])[CH:13]=2)=[C:6]([C:26]2[CH:31]=[C:30]([C:32](=[O:44])[NH:33][C@@H:34]3[C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH2:37][CH2:36][CH2:35]3)[CH:29]=[CH:28][N:27]=2)[CH:5]=1)[CH3:2].[N:47]1([C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[CH2:53][CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1.CC(O)=O.C([BH3-])#N.[Na+]>C(O)C.C(OCC)(=O)C>[CH2:45]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:12]2[CH:13]=[C:14]([CH:22]=[CH:23][CH:24]=2)[C:15]([N:17]([CH2:18][CH2:19][N:50]2[CH2:51][CH2:52][CH2:53][N:47]([C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[CH2:48][CH2:49]2)[CH3:21])=[O:16])=[O:25])=[C:6]([C:26]2[CH:31]=[C:30]([C:32](=[O:44])[NH:33][C@@H:34]3[C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH2:37][CH2:36][CH2:35]3)[CH:29]=[CH:28][N:27]=2)[CH:5]=1)[CH3:46]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 86705976(S)-N-(4-(diethylamino)-2-(4-((1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyridin-2-yl)phenyl)-N3-methyl-N3-(2-oxoethyl)isophthalamide

Produkt 1

HCID 68087739(S)-tert-butyl 4-(2-(3-((4-(diethylamino)-2-(4-((1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl) pyridin-2-yl)phenyl)carbamoyl)-N-methylbenzamido)ethyl)-1,4-diazepane-1-carboxylateAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of (S)—N1-(4-(diethylamino)-2-(4-((1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyridin-2-yl)phenyl)-N3-methyl-N3-(2-oxoethyl)isophthalamide (0.162 mmol, 100 mg) in ethanol (1 mL) were added tert-butyl 1,4-diazepane-1-carboxylate (0.324 mmol, 65 mg) and HOAc (0.324 mmol, 19.4 mg). The mixture was stirred at room temperature for 20 minutes, and then sodium cyanoborohydride (0.81 mmol, 51 mg) was added. The mixture was stirred for an additional 1 h, diluted with ethyl acetate, washed with sat. aqueous NaHCO3 and brine, dried, concentrated and purified by column to give a product (70 mg, 54%).

Aufarbeitung

  1. stirringThe mixture was stirred for an additional 1 h
  2. washwashed with sat. aqueous NaHCO3 and brine
  3. customdried
  4. concentrationconcentrated
  5. custompurified by column

Quellen und Nachweise

ORD-Eintrag
ord-52a329009e4648f1a311d491906f55ae
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08916569B2

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