Cyclobutylamine → HCID 16036916, compound

HRID 1806250Notes

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][CH:24]=[C:23]([CH:27]=O)[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.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[CH:32]1([NH:36][CH2:27][C:23]2[CH:22]=[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[CH2:8][CH2:7][N:6]([S:3]([CH2:1][CH3:2])(=[O:4])=[O:5])[CH2:11][CH2:10]3)[CH:26]=[CH:25][CH:24]=2)[CH2:35][CH2:34][CH2:33]1

Participants

Reactant 3

HCID 75645Cyclobutylamine

HCID 5049666Sodium triacetoxyborohydride

HCID 577328043-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide

Product 1

HCID 16036916HCID 16036916, compoundYield 35%

Procedure

Following the general procedure of example 31, 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide (50 mg, 0.113 mmol), cyclobutanamine (24.1 mg, 0.339 mmol) and NaBH(OAc)3 (75 mg, 0.545 mmol) were reacted to give the title compound (19.3 mg, 35%).

Workup

customwere reacted

Sources & evidence

ORD record: ord-d1e80fa8941b490db2f6f5203e8e542a
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354406B2

Reaction notes

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