Triethylamine → HCID 57732842, compound

HRID 1806518Notes

Reaction equation

HRID 1806518 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:25]=[C:24]([CH2:26][NH:27][CH3:28])[S:23][CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].C(N(CC)CC)C.[CH3:39][CH2:40][O:41][C:42](Cl)=[O:43]>CN(C=O)C>[NH2:31][C:29]([C:16]1[CH:17]=[C:18]([C:21]2[CH:25]=[C:24]([CH2:26][N:27]([CH3:28])[C:42](=[O:43])[O:41][CH2:40][CH3:39])[S:23][CH:22]=2)[CH:19]=[C:20]2[C:15]=1[NH:14][CH:13]=[C:12]2[CH:9]1[CH2:10][CH2:11][N:6]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH2:7][CH2:8]1)=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 42629297HCID 42629297, compound

Product 1

HCID 57732842HCID 57732842, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-{5-[(methylamino)methyl]-3-thienyl}-1H-indole-7-carboxamide (50 mg, 0.11 mmol) in DMF (1.0 mL) at 0° C. was added triethylamine (0.06 mL, 0.44 mmol), and ethyl chloridocarbonate (0.021 mL, 0.22 mmol). The resultant mixture was reacted for 30 min followed by purification on Gilson Preparatory HLPC to afford 31.4 mg of the title compound (53.5%).

Workup

  1. customfollowed by purification on Gilson Preparatory HLPC

Sources & evidence

ORD record
ord-b1a780bd17084c819f17c071047218d6
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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