Cyclopropanecarbonyl chloride → HCID 118079380, compound

HRID 1485724Notes

Reaction equation

HRID 1485724 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.[CH:37]1([C:40](Cl)=[O:41])[CH2:39][CH2:38]1>ClCCCl>[CH:37]1([C:40]([N:22]2[C:21]3[C:26](=[CH:27][C:18]([C:16]4[CH:15]=[N:14][N:13]([CH:10]5[CH2:12][CH2:11]5)[CH:17]=4)=[CH:19][CH:20]=3)[N:25]([C:28]([O:30][CH:31]3[CH2:32][CH2:33][CH2:34][CH2:35]3)=[O:29])[CH2:24][C@@H:23]2[CH3:36])=[O:41])[CH2:39][CH2:38]1

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 118078898HCID 118078898, compound

Product 1

HCID 118079380HCID 118079380, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

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 cyclopropanecarbonyl chloride (0.077 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)-cyclopentyl 4-(cyclopropanecarbonyl)-7-(1-cyclopropyl-1H-pyrazol-4-yl)-3-methyl-3,4-dihydroquinoxaline-1(2H)-carboxylate (0.056 g, 76%) as a an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.71-0.91 (m, 3 H), 0.93-1.12 (m, 8 H), 1.48-1.99 (m, 9 H), 3.42-3.55 (m, 1 H), 3.75 (tt, J=7.33, 3.81 Hz, 1 H), 3.93 (br dd, J=12.75, 6.30 Hz, 1 H), 4.86-4.98 (m, 1 H), 5.14 (td, J=5.50, 2.79 Hz, 1 H), 7.29-7.44 (m, 2 H), 7.76 (s, 1 H), 7.91 (s, 1 H), 8.17 (s, 1 H). MS (ESI, pos. ion) m/z 435 [M+1]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto afford a brown oil
  3. 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-00543b9b34c9468da79ae13b78249a56
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

Loading…