Isopropyl chloroformate → HCID 118079663, compound

HRID 1485727Notes

Reaction equation

HRID 1485727 reaction equation
FC(F)(F)C=O.[CH:7]1([N:10]2[CH:14]=[C:13]([C:15]3[CH:16]=[C:17]4[C:22](=[CH:23][CH:24]=3)[N:21]([C:25]([O:27][CH3:28])=[O:26])[C@@H:20]([CH3:29])[CH2:19][N:18]4[C:30]([O:32][CH:33]3[CH2:37]CC[CH2:34]3)=[O:31])[CH:12]=[N:11]2)[CH2:9][CH2:8]1.ClC(OC(C)C)=O>>[CH:7]1([N:10]2[CH:14]=[C:13]([C:15]3[CH:16]=[C:17]4[C:22](=[CH:23][CH:24]=3)[N:21]([C:25]([O:27][CH3:28])=[O:26])[C@@H:20]([CH3:29])[CH2:19][N:18]4[C:30]([O:32][CH:33]([CH3:37])[CH3:34])=[O:31])[CH:12]=[N:11]2)[CH2:8][CH2:9]1

Participants

4

Reactant 3

HCID 7917Isopropyl chloroformateHCID 65564TrifluoroacetaldehydeHCID 118079076HCID 118079076, compound

Product 1

HCID 118079663HCID 118079663, compound

Procedure

(S)-4-isopropyl 1-methyl 6-(1-cyclopropyl-1H-pyrazol-4-yl)-2-methyl-2,3-dihydroquinoxaline-1,4-dicarboxylate was prepared from 2-methyl-3,4-dihydroquinoxalin-1(2H)-yl)-2,2,2-trifluoroethanone following the procedure outlined above for (S)-4-cyclopentyl 1-methyl 6-(1-cyclopropyl-1H-pyrazol-4-yl)-2-methyl-2,3-dihydroquinoxaline-1,4-dicarboxylate and substituting isopropyl chloroformate (1.0 M solution in toluene) in Step 1. The desired product was obtained as an off-white solid (0.065 g, 79%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.90-1.03 (m, 2 H), 1.07 (br d, J=6.16 Hz, 5 H), 1.26 (dd, J=5.86, 2.93 Hz, 6 H), 3.60-3.83 (m, 6 H), 4.49-4.71 (m, 1 H), 4.93 (dt, J=12.46, 6.08 Hz, 1 H), 7.28 (br d, J=7.04 Hz, 1 H), 7.65-7.87 (m, 3 H), 8.14 (s, 1 H). MS (ESI, pos. ion) m/z 399 [M+1]+.

Sources & evidence

ORD record
ord-264c36e1e85147aba14282d6ddbfb784
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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