Methyl chloroformate → HCID 118079076, compound

HRID 1485723Notes

Reaction equation

C(N(CC)C(C)C)(C)C.[CH:10]1([N:13]2[CH:17]=[C:16]([C:18]3[CH:27]=[C:26]4[C:21]([NH:22][C@@H:23]([CH3:36])[CH2:24][N:25]4[C:28]([O:30][CH:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)=[O:29])=[CH:20][CH:19]=3)[CH:15]=[N:14]2)[CH2:12][CH2:11]1.Cl[C:38]([O:40][CH3:41])=[O:39]>ClCCCl>[CH:10]1([N:13]2[CH:17]=[C:16]([C:18]3[CH:27]=[C:26]4[C:21](=[CH:20][CH:19]=3)[N:22]([C:38]([O:40][CH3:41])=[O:39])[C@@H:23]([CH3:36])[CH2:24][N:25]4[C:28]([O:30][CH:31]3[CH2:32][CH2:33][CH2:34][CH2:35]3)=[O:29])[CH:15]=[N:14]2)[CH2:12][CH2:11]1

Participants

Conditions

Temperature: 50 °C

Procedure

N,N-Diisopropylethylamine (0.148 mL, 0.846 mmol) was added to a solution of (S)-cyclopentyl 7-(1-cyclopropyl-1H-pyrazol-4-yl)-3-methyl-3,4-dihydroquinoxaline-1(2H)-carboxylate (0.062 g, 0.169 mmol) and methyl chloroformate (0.065 mL, 0.846 mmol) in 1,2-dichloroethane (2.0 mL), and the mixture stirred at 50° C. for 2.5 h. The reaction mixture was concentrated to afford a brown oil. This material was purified via column chromatography on silica gel (Biotage 25 g column, gradient elution with 0-50% ethyl acetate-hexane) to afford (S)-4-cyclopentyl 1-methyl 6-(1-cyclopropyl-1H-pyrazol-4-yl)-2-methyl-2,3-dihydroquinoxaline-1,4-dicarboxylate (0.057 g, 79%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.90-1.02 (m, 2 H), 1.02-1.12 (m, 5 H), 1.37-1.93 (m, 9 H), 3.66-3.81 (m, 5 H), 4.49-4.72 (m, 1 H), 5.00-5.21 (m, 1 H), 7.17-7.39 (m, 1 H), 7.67-7.82 (m, 3 H), 8.13 (s, 1 H). MS (ESI, pos. ion) m/z 425. [M+1]+.

Workup

concentrationThe reaction mixture was concentrated
customto afford a brown oil
customThis material was purified via column chromatography on silica gel (Biotage 25 g column, gradient elution with 0-50% ethyl acetate-hexane)

Sources & evidence

ORD record: ord-68e17fc517744609aa5586b38d1eb527
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422281B2

Reaction notes

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