Dichloromethane → HCID 57970677, compound

HRID 1639976Notes

Reaction equation

Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH2:29][CH2:28][CH2:27][C@@:15]3([C:19](=[O:20])[N:18]([CH:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[CH2:17][CH2:16]3)[CH2:14]2)=[N:11][CH:12]=1.C(N(CC)C(C)C)(C)C.C(Cl)Cl>>[CH3:5][O:4][C:2](=[O:3])[NH:6][C:7]1[CH:12]=[N:11][C:10]([N:13]2[CH2:29][CH2:28][CH2:27][C@@:15]3([C:19](=[O:20])[N:18]([CH:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)[CH2:17][CH2:16]3)[CH2:14]2)=[CH:9][CH:8]=1

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 6586Methyl chloroformate

HCID 81531Diisopropylethylamine

HCID 66722463HCID 66722463, compound

Product 1

HCID 57970677HCID 57970677, compound

Procedure

Methyl chloroformate (4.4 μL, 0.000057 mol) was added to a solution of (5S)-7-(5-aminopyridin-2-yl)-2-(tetrahydro-2H-pyran-4-yl)-2,7-diazaspiro[4.5]decan-1-one (15.8 mg, 0.0000478 mol), N,N-diisopropylethylamine (27 μL, 0.00016 mol) and methylene chloride (1.0 mL, 0.016 mol); and the mixture was stirred for 1 h. The volatiles were removed in-vacuo and the crude product was purified by prep-HPLC. LC-MS: 389.2 (M+H)+.

Workup

customThe volatiles were removed in-vacuo
customthe crude product was purified by prep-HPLC

Sources & evidence

ORD record: ord-f99589d3fe3145d2a581ec2bf1cc3da4
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110581B2

Reaction notes

Loading…