Acetic Acid → HCID 59722620, compound

HRID 1664841Notes

Reaction equation

HRID 1664841 reaction equation
C([BH3-])#N.[Na+].[F:5][C:6]1[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:7]=1[C@H:13]1[CH2:19][N:18]2[C:20]([CH2:23][CH:24]=O)=[CH:21][N:22]=[C:17]2[C@H:16]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:15][CH2:14]1.[CH3:34][NH:35][CH3:36].C(O)(=O)C>CO>[F:5][C:6]1[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:7]=1[C@H:13]1[CH2:19][N:18]2[C:20]([CH2:23][CH2:24][N:35]([CH3:36])[CH3:34])=[CH:21][N:22]=[C:17]2[C@H:16]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:30])[CH3:31])[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 5003444Sodium cyanoborohydrideHCID 59722591HCID 59722591, compound

Product 1

HCID 59722620HCID 59722620, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (12 mg, 0.185 mmol) was added to a solution of tert-butyl (6S,9R)-6-(2,3-difluorophenyl)-3-(2-oxoethyl)-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-ylcarbamate (50 mg, 0.123 mmol) and dimethylamine (2.0 M in tetrahydrofuran; 0.185 mL, 0.370 mmol) in methanol (5 mL) adjusted to pH 5 with acetic acid. After 2 h, the solution was concentrated. Purification by silica gel chromatography (100% dichloromethane→92% dichloromethane/methanol) gave the title compound (45 mg). MS 435.2 (M+1).

Workup

  1. concentrationthe solution was concentrated
  2. customPurification by silica gel chromatography (100% dichloromethane→92% dichloromethane/methanol)

Sources & evidence

ORD record
ord-91353b4e75aa48318b72f4cc9d16170c
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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