Sodium borohydride → HCID 178418908, compound

HRID 7164

Reaction equation

HRID 7164 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[N:2]1.[NH2:8][CH2:9][C:10]1[CH:37]=[CH:36][C:13]([CH2:14][N:15]([CH2:26][C:27]2[NH:31][C:30]3[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=3[N:28]=2)[CH:16]2[C:25]3[N:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH2:19][CH2:18][CH2:17]2)=[CH:12][CH:11]=1.[BH4-].[Na+]>CO>[NH:28]1[C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=[C:27]1[CH2:26][N:15]([CH2:14][C:13]1[CH:36]=[CH:37][C:10]([CH2:9][NH:8][CH2:6][C:3]2[CH:4]=[CH:5][NH:1][N:2]=2)=[CH:11][CH:12]=1)[CH:16]1[C:25]2[N:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 122183831H-Pyrazole-3-carbaldehydeHCID 21985008N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amine

Product 1

HCID 178418908HCID 178418908, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using General Procedure B: A solution of pyrazol-3-carboxaldehyde (26.6 mg, 0.28 mmol) and (4-aminomethyl-benzyl)-(1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (110 mg, 0.28 mmol) in MeOH (2.0 mL) was stirred overnight at room temperature. NaBH4 (21.2 mg, 0.56 mmol) was added and the resultant mixture stirred for an additional 15 minutes. Purification by column chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 100:1:1) afforded the desired amine (80 mg, 60%) as a white foam.

Workup

  1. customPurification by column chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 100:1:1)

Sources & evidence

ORD record
ord-0911da83313443a48e5e67c1ea659593
Source dataset
uspto-grants-2006_08
Patent number
US07084155B2

Linked notes

Loading…