Ammonia → HCID 21925576, compound

HRID 2118056Notes

Reaction equation

C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:15][C:16]1[CH:41]=[CH:40][C:19]2[N:20]3[C:24]([CH2:25][NH:26][CH2:27][C:18]=2[CH:17]=1)=[N:23][N:22]=[C:21]3[CH:28]1[CH2:33][CH2:32][N:31]([C:34]2[N:39]=[CH:38][CH:37]=[CH:36][N:35]=2)[CH2:30][CH2:29]1.[N:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[CH:48]=O.N>C(O)(=O)C.ClCCl>[Cl:15][C:16]1[CH:41]=[CH:40][C:19]2[N:20]3[C:24]([CH2:25][N:26]([CH2:48][C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][N:42]=4)[CH2:27][C:18]=2[CH:17]=1)=[N:23][N:22]=[C:21]3[CH:28]1[CH2:33][CH2:32][N:31]([C:34]2[N:35]=[CH:36][CH:37]=[CH:38][N:39]=2)[CH2:30][CH2:29]1

Participants

Conditions

Temperature: 5 °C

Procedure

Sodium triacetoxyborohydride (277 mg, 1.31 mmol) was added to a mixture of the amine from example 12 (250 mg, 0.65 mmol), 2-pyridine carboxaldehyde (105 mg, 0.98 mmol), and acetic acid (3 drops) in dichloromethane (5 ml), cooled to 5° C., and the reaction mixture was then stirred at room temperature for 18 hours. 0.88 Ammonia was added to the reaction mixture, the phases were separated and the organic layer was dried over magnesium sulphate and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using dichloromethane:methanol (95:5) as eluant, to afford the title compound (167 mg)

Workup

customthe phases were separated
dry with materialthe organic layer was dried over magnesium sulphate
customevaporated under reduced pressure
customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-10745ed9a2bc4e398563f74dcfbbb861
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442795B2

Reaction notes

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