Sodium borohydride → HCID 178419093, compound

HRID 7165

Reaction equation

HRID 7165 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([CH:7]=O)[N:6]=1.[NH2:9][CH2:10][C:11]1[CH:38]=[CH:37][C:14]([CH2:15][N:16]([CH2:27][C:28]2[NH:32][C:31]3[CH:33]=[CH:34][CH:35]=[CH:36][C:30]=3[N:29]=2)[CH:17]2[C:26]3[N:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH2:20][CH2:19][CH2:18]2)=[CH:13][CH:12]=1.[BH4-].[Na+]>CO>[NH:32]1[C:31]2[CH:33]=[CH:34][CH:35]=[CH:36][C:30]=2[N:29]=[C:28]1[CH2:27][N:16]([CH2:15][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][NH:9][CH2:7][C:5]2[N:6]=[C:2]([CH3:1])[NH:3][CH:4]=2)=[CH:38][CH:37]=1)[CH:17]1[C:26]2[N:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21985008N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amineHCID 178418999HCID 178418999, compound

Product 1

HCID 178419093HCID 178419093, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using General Procedure B: A solution of 2-methyl-1H-imidazole-4-carbaldehyde (27.7 mg, 0.25 mmol) and (4-aminomethyl-benzyl)-(1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (100 mg, 0.25 mmol) in MeOH (2.0 mL) was stirred overnight at room temperature. NaBH4 (18.9 mg, 0.50 mmol) was added and the resultant mixture stirred for an additional 15 minutes. Purification of the crude yellow foam by column chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 200:3:3) afforded the desired amine (65 mg, 53%) as a white foam.

Workup

  1. customPurification of the crude yellow foam by column chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 200:3:3)

Sources & evidence

ORD record
ord-8ab4549260ae492c980f2cd8534f6614
Source dataset
uspto-grants-2006_08
Patent number
US07084155B2

Linked notes

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