Cyclopropanecarbonyl chloride → HCID 59612368, compound

HRID 1890012Notes

Reaction equation

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

Participants

Reactant 2

HCID 77637Cyclopropanecarbonyl chloride

HCID 67478812HCID 67478812, compound

Product 1

HCID 59612368HCID 59612368, compound

Procedure

Cyclopropanecarboxylic acid [8-(2-Methoxy-5-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-2-yl]-amide was prepared from 8-(2-methoxy-5-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-2yl-amine (0.07 g, 0.2 mmol) and cyclopropanecarbonyl chloride (0.021 mL, 0.23 mmol) in a manner analogous to Example 240b. Product was isolated as a foam (0.063 g, 70%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.61 (d, J=6.7 Hz, 1H), 7.76-7.66 (m, 2H), 7.60-7.50 (m, 1H), 7.51-7.45 (m, 1H), 7.13-7.06 (m, 1H), 3.86 (s, 3H), 1.56 (m, 1H), 1.19-1.14 (m, 2H), 1.01-0.95 (m, 2H), MS=377 (MH)+.

Sources & evidence

ORD record: ord-1a2b900355b841e9b14e73f2c533f5cf
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501936B2

Reaction notes

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