Diisopropylethylamine → HCID 57732731, compound

HRID 562294Notes

Reaction equation

HRID 562294 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]3[C:15](=[C:16]([C:18]([NH2:20])=[O:19])[CH:17]=2)[NH:14][CH:13]=[C:12]3[CH:21]2[CH2:26][CH2:25][N:24]([S:27]([CH2:30][CH3:31])(=[O:29])=[O:28])[CH2:23][CH2:22]2)[CH:6]=[CH:7][CH:8]=1.[CH:32]1([S:35](Cl)(=[O:37])=[O:36])[CH2:34][CH2:33]1.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[CH:32]1([S:35]([NH:1][CH2:2][C:3]2[CH:4]=[C:5]([C:9]3[CH:10]=[C:11]4[C:15](=[C:16]([C:18]([NH2:20])=[O:19])[CH:17]=3)[NH:14][CH:13]=[C:12]4[CH:21]3[CH2:22][CH2:23][N:24]([S:27]([CH2:30][CH3:31])(=[O:29])=[O:28])[CH2:25][CH2:26]3)[CH:6]=[CH:7][CH:8]=2)(=[O:37])=[O:36])[CH2:34][CH2:33]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2760919Cyclopropanesulfonyl chlorideHCID 16038109HCID 16038109, compound

Product 1

HCID 57732731HCID 57732731, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[3-(aminomethyl)phenyl]-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide (35 mg, 0.079 mmol) in DMF (1.0 mL) and DCM (1.0 mL) was added cyclopropanesulfonyl chloride (11 mg, 0.079 mmol) and DIEA (14 μL, 0.079 mmol). Reaction was stirred at room temperature overnight. Compound was purified by Gilson Preparatory HPLC to give 7.2 mg the title compound (17%).

Workup

  1. customReaction
  2. customCompound was purified by Gilson Preparatory HPLC

Sources & evidence

ORD record
ord-de3c6bf48c1c4e0b9be464f98cbafa12
Source dataset
uspto-grants-2011_11
Patent number
US08063071B2

Reaction notes

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