Diethylamine → HCID 57732845, compound

HRID 1806310Notes

Reaction equation

HRID 1806310 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][C:24]([CH:27]=O)=[CH:23][CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].[CH2:32]([NH:34][CH2:35][CH3:36])[CH3:33].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CS(C)=O.C(O)(=O)C>[CH2:32]([N:34]([CH2:27][C:24]1[CH:25]=[CH:26][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:4])=[O:5])[CH2:7][CH2:8]2)=[CH:22][CH:23]=1)[CH2:35][CH3:36])[CH3:33]

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 57732795HCID 57732795, compound

Product 1

HCID 57732845HCID 57732845, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(4-formylphenyl)-1H-indole-7-carboxamide (50 mg, 0.114 mmol) in DMSO (3 mL) and acetic acid was added diethylamine (36 μL, 0.342 mmol). After 2 h, sodium triacetoxyborohydride (290 mg, 1.36 mmol) was added. Reaction mixture was stirred overnight. Compound was purified by Gilson Preparatory HPLC to afford 37.6 mg of the title compound (67%).

Workup

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

Sources & evidence

ORD record
ord-e8b0003c430e4f49a58764bba7348246
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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