Tert-Butylamine → 5-(5-{[(1,1-dimethylethyl)amino]methyl}-3-thienyl)-3-(1-{[3-(methyloxy)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide

HRID 2267591Notes

Reaction equation

HRID 2267591 reaction equation
[CH:1]([C:3]1[S:7][CH:6]=[C:5]([C:8]2[CH:9]=[C:10]3[C:14](=[C:15]([C:17]([NH2:19])=[O:18])[CH:16]=2)[NH:13][CH:12]=[C:11]3[CH:20]2[CH2:25][CH2:24][N:23]([S:26]([CH2:29][CH2:30][CH2:31][O:32][CH3:33])(=[O:28])=[O:27])[CH2:22][CH2:21]2)[CH:4]=1)=O.[CH3:34][C:35]([NH2:38])([CH3:37])[CH3:36].[BH4-].[Na+]>>[CH3:34][C:35]([NH:38][CH2:1][C:3]1[S:7][CH:6]=[C:5]([C:8]2[CH:9]=[C:10]3[C:14](=[C:15]([C:17]([NH2:19])=[O:18])[CH:16]=2)[NH:13][CH:12]=[C:11]3[CH:20]2[CH2:21][CH2:22][N:23]([S:26]([CH2:29][CH2:30][CH2:31][O:32][CH3:33])(=[O:27])=[O:28])[CH2:24][CH2:25]2)[CH:4]=1)([CH3:37])[CH3:36]

Participants

4

Reactant 3

HCID 6385Tert-ButylamineHCID 4311764Sodium borohydrideHCID 116201055-(5-formyl-3-thienyl)-3-(1-{[3-(methyloxy)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide

Product 1

HCID 590033035-(5-{[(1,1-dimethylethyl)amino]methyl}-3-thienyl)-3-(1-{[3-(methyloxy)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide

Procedure

Following the general procedure in example 281, 5-(5-formyl-3-thienyl)-3-(1-{[3-(methyloxy)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide (40 mg, 0.08 mmol), (1,1-dimethylethyl)amine (70 mg, 0.8 mmol) and NaBH4 (30.26 mg, 0.8 mmol) were reacted to form the desired product which was purified by Gilson HPLC (CH3CN/Water, 0.1% TFA) (8.4 mg, 19%).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-505aa8c8663747f6b58a09a69ceb66ef
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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