Formaldehyde → 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-{[[2-(ethylthio)ethyl](methyl)amino]methyl}-3-thienyl)-1H-indole-7-carboxamide

HRID 1806517Notes

Reaction equation

HRID 1806517 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]([CH:29](C)[CH3:30])(=[O:28])=[O:27])[CH2:22][CH2:21]2)[CH:4]=1)=O.[CH2:32]([S:34][CH2:35][CH2:36][NH2:37])[CH3:33].[C:38](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([BH3-])#N.[Na+].C=O>CS(C)=O.C(O)(=O)C>[CH2:29]([S:26]([N:23]1[CH2:22][CH2:21][CH:20]([C:11]2[C:10]3[C:14](=[C:15]([C:17]([NH2:19])=[O:18])[CH:16]=[C:8]([C:5]4[CH:4]=[C:3]([CH2:1][N:37]([CH2:36][CH2:35][S:34][CH2:32][CH3:33])[CH3:38])[S:7][CH:6]=4)[CH:9]=3)[NH:13][CH:12]=2)[CH2:25][CH2:24]1)(=[O:27])=[O:28])[CH3:30]

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 148011Ethanamine, 2-(ethylthio)-HCID 5003444Sodium cyanoborohydrideHCID 5049666Sodium triacetoxyborohydrideHCID 577327835-(5-formyl-3-thienyl)-3-{1-[(1-methylethyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide

Product 1

HCID 577328503-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-{[[2-(ethylthio)ethyl](methyl)amino]methyl}-3-thienyl)-1H-indole-7-carboxamideYield 14.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 5-(5-formyl-3-thienyl)-3-{1-[(1-methylethyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide (40 mg, 0.09 mmol) in DMSO (2 mL) was added [2-(ethylthio)ethyl]amine (105 mg, 1 mmol), acetic acid (50 μL), and sodium triacetoxyborohydride (212 mg, 1.0 mmol). The resulting mixture was stirred overnight. To the mixture was added sodium cyanoborohydride (80 mg, 1.2 mmol) and stirred overnight followed by addition of formaldehyde (100 μL, 1.2 mmol). The mixture was then stirred for an additional 3 h. It was then purified by Gilson Preparatory HPLC to give 7.0 mg of the title compound.

Workup

  1. stirringstirred overnight
  2. stirringThe mixture was then stirred for an additional 3 h
  3. customIt was then purified by Gilson Preparatory HPLC

Sources & evidence

ORD record
ord-6f498d7b521c406a961dc2bd271791d6
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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