Bis(2-Methoxyethyl)amine → HCID 16038008, compound

HRID 1806227Notes

Reaction equation

HRID 1806227 reaction equation
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:29]([NH2:31])=[O:30])[CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]=O)[CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].[CH3:32][O:33][CH2:34][CH2:35][NH:36][CH2:37][CH2:38][O:39][CH3:40].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[CH3:32][O:33][CH2:34][CH2:35][N:36]([CH2:27][C:23]1[CH:22]=[C:21]([C:18]2[CH:19]=[C:20]3[C:15](=[C:16]([C:29]([NH2:31])=[O:30])[CH:17]=2)[NH:14][CH:13]=[C:12]3[CH:9]2[CH2:10][CH2:11][N:6]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH2:7][CH2:8]2)[CH:26]=[CH:25][CH:24]=1)[CH2:37][CH2:38][O:39][CH3:40]

Participants

4

Reactant 3

HCID 2383Bis(2-Methoxyethyl)amineHCID 5049666Sodium triacetoxyborohydrideHCID 577328043-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide

Product 1

HCID 16038008HCID 16038008, compoundYield 16.8%

Procedure

Following the general procedure of example 1, 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide (50.0 mg, 0.112 mmol), 2-(methyloxy)-N-[2-(methyloxy)ethyl]ethanamine (114.3 mg, 0.86 mmol) and NaBH(OAc)3 (58.0 mg, 0.303 mmol) were reacted to give the title compound (10.5 mg, 16%).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-798afe98ada74b45b631ef824b099b7a
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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