Acetic Acid → (1H-benzimidazol-2-ylmethyl)-[4-(3,4-dihydro-1H-isoquinolin-2-ylmethyl)-benzyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

HRID 7181

Reaction equation

HRID 7181 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.[NH:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[CH2:20][N:21]([CH2:32][C:33]1[CH:40]=[CH:39][C:36]([CH:37]=O)=[CH:35][CH:34]=1)[CH:22]1[C:31]2[N:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH2:25][CH2:24][CH2:23]1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1>[NH:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[CH2:20][N:21]([CH2:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37][N:2]2[CH2:3][CH2:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:1]2)=[CH:35][CH:34]=1)[CH:22]1[C:31]2[N:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 70461,2,3,4-TetrahydroisoquinolineHCID 5049666Sodium triacetoxyborohydrideHCID 219849824-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzaldehyde

Product 1

HCID 22018845(1H-benzimidazol-2-ylmethyl)-[4-(3,4-dihydro-1H-isoquinolin-2-ylmethyl)-benzyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amineYield 78.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using General Procedure B: To a stirred solution of 1,2,3,4-tetrahydroisoquinoline (49 mg, 0.37 mmol), 4-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzaldehyde (140 mg, 0.34 mmol), and AcOH 0.020 mL, 0.35 mmol) in THF (3.5 mL) was added NaBH(OAc)3 (94 mg, 0.44 mmol) and the mixture was stirred at room temperature for 2 h. Purification of the crude material by column chromatography on silica gel (500:5:1 CH2Cl2/MeOH/NH4OH) afforded a colourless foam (137 mg).

Workup

  1. customPurification of the crude material by column chromatography on silica gel (500:5:1 CH2Cl2/MeOH/NH4OH)

Sources & evidence

ORD record
ord-d3399affb5e9484d901d531f62b141b6
Source dataset
uspto-grants-2006_08
Patent number
US07084155B2

Linked notes

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