Isopropyl chloroformate → HCID 86701969, compound

HRID 715791Notes

Reaction equation

HRID 715791 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12]([C:14]3[S:15][C:16]([CH:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)=[CH:17][CH:18]=3)=[O:13])=[CH:6][C:5]=12.CN1CCOCC1.[CH:32]([O:35][C:36](Cl)=[O:37])([CH3:34])[CH3:33]>ClCCl>[CH3:33][CH:32]([O:35][C:36]([N:22]1[CH2:23][CH2:24][CH:19]([C:16]2[S:15][C:14]([C:12](=[O:13])[NH:11][CH2:10][C:7]3[CH:8]=[CH:9][N:4]4[CH:3]=[CH:2][N:1]=[C:5]4[CH:6]=3)=[CH:18][CH:17]=2)[CH2:20][CH2:21]1)=[O:37])[CH3:34]

Participants

5

Reactant 3

HCID 7917Isopropyl chloroformate2×HCID 79724-MethylmorpholineHCID 86701970HCID 86701970, compound

Product 1

HCID 86701969HCID 86701969, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide (0.103 g, 0.249 mmol) in dichloromethane (2 ml) was added N-methylmorpholine (0.110 ml, 0.997 mmol) followed by isopropylchloroformate (0.374 ml, 0.374 mmol). A second portion of isopropylchloroformate (0.4 ml) was added and after 1 hour the mixture was directly purified by normal phase chromatography to give the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.05 (t, J=6.0 Hz, 1H), 8.51 (d, J=7.0 Hz, 1H), 7.92 (s, 1H), 7.68 (d, J=3.8 Hz, 1H), 7.56 (d, J=1.2 Hz, 1H), 7.40 (d, J=1.4 Hz, 1H), 6.96 (d, J=3.8 Hz, 1H), 6.88 (dd, J=7.0, 1.7 Hz, 1H), 4.78 (hept, J=6.2 Hz, 1H), 4.47 (d, J=5.9 Hz, 2H), 4.05 (d, J=12.9 Hz, 2H), 3.10-2.97 (m, 1H), 2.98-2.81 (m, 2H), 2.01-1.88 (m, 2H), 1.57-1.38 (m, 2H), 1.19 (d, J=6.2 Hz, 6H); MS (ESI(+)) m/e 427 (M+H)+.

Workup

  1. customwas directly purified by normal phase chromatography

Sources & evidence

ORD record
ord-332dcae450e04cd9bd844d01af5ed6e3
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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