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Dimethylamine → 5-[3-[(dimethylamino)methyl]-4,5-bis(methyloxy)phenyl]-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide

HRID 562078
Notes
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Reaction equation

HRID 562078 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:33]([NH2:35])=[O:34])[CH:17]=[C:18]([C:21]4[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([CH:31]=O)[CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].C([BH3-])#N.[Na+].[CH3:40][NH:41][CH3:42]>CO.[Cl-].[Zn+2].[Cl-]>[CH3:40][N:41]([CH2:31][C:23]1[CH:22]=[C:21]([C:18]2[CH:19]=[C:20]3[C:15](=[C:16]([C:33]([NH2:35])=[O:34])[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]=[C:25]([O:27][CH3:28])[C:24]=1[O:29][CH3:30])[CH3:42]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 674DimethylamineHCID 5003444Sodium cyanoborohydrideHCID 866310263-[1-(ethylsulfonyl)-4-piperidinyl]-5-[3-formyl-4,5-bis(methyloxy)phenyl]-1H-indole-7-carboxamide

Product 1

HCID 160373075-[3-[(dimethylamino)methyl]-4,5-bis(methyloxy)phenyl]-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamideYield 34.7%

Reagents, catalysts & solvents 2

HCID 3007855
Zincchloride
Catalyst
HCID 887MethanolSolvent

Procedure

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-[3-formyl-4,5-bis(methyloxy)phenyl]-1H-indole-7-carboxamide (30 mg, 0.06 mmol) in methanol (2 mL), zinc chloride (5 mg, 0.03 mmol), sodium cyanoborohydride (5 mg, 0.06 mmol) and dimethylamine (100 μL, 0.30 mmol). The mixture was stirred at room temperature for 2 h then reacted in the microwave at 100° C. for 30 min. The resulting mixture was purified by Gilson Preparatory HPLC to give 11 mg of the title compound (34.7%).

Workup

  1. customthen reacted in the microwave at 100° C. for 30 min
  2. customThe resulting mixture was purified by Gilson Preparatory HPLC

Sources & evidence

ORD record
ord-183e7fbbf1ee4c4080ed6a87f935c278
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08063071B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes