Cyclobutylamine → HCID 57732738, compound

HRID 1806308Notes

Reaction equation

HRID 1806308 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].[CH:32]1([NH2:36])[CH2:35][CH2:34][CH2:33]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CS(C)=O.C(O)(=O)C>[CH:32]1([NH:36][CH2:27][C:24]2[CH:25]=[CH:26][C:21]([C:18]3[CH:19]=[C:20]4[C:15](=[C:16]([C:29]([NH2:31])=[O:30])[CH:17]=3)[NH:14][CH:13]=[C:12]4[CH:9]3[CH2:10][CH2:11][N:6]([S:3]([CH2:1][CH3:2])(=[O:4])=[O:5])[CH2:7][CH2:8]3)=[CH:22][CH:23]=2)[CH2:35][CH2:34][CH2:33]1

Participants

6

Reactant 3

HCID 75645CyclobutylamineHCID 5049666Sodium triacetoxyborohydrideHCID 57732795HCID 57732795, compound

Product 1

HCID 57732738HCID 57732738, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(4-formylphenyl)-1H-indole-7-carboxamide (40 mg, 0.091 mmol) in DMSO (900 μL) and acetic acid (2 drops) was added cyclobutylamine (94 μL, 1.08 mmol). After 2 h, sodium triacetoxyborohydride (120 mg, 1.10 mmol) was added. Reaction mixture was stirred overnight. Compound was purified by Gilson Preparatory HPLC to afford 26.3 mg of the title compound (59%).

Workup

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

Sources & evidence

ORD record
ord-d30fc090c97d4a7ba27ce9df63877402
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

Loading…