Cyclopropanecarbonyl chloride → HCID 136245973, compound

HRID 59482Notes

Reaction equation

HRID 59482 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([Cl:35])=[C:7]([C:9]2[NH:13][C:12](=[O:14])[N:11]([C:15]3[CH:32]=[CH:31][C:18]([C:19]([NH:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]([F:30])[F:29])[CH:23]=4)=[O:20])=[C:17]([O:33][CH3:34])[CH:16]=3)[N:10]=2)[CH:8]=1.[CH:36]1([C:39](Cl)=[O:40])[CH2:38][CH2:37]1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:35][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][NH:1][C:39]([CH:36]2[CH2:38][CH2:37]2)=[O:40])=[CH:8][C:7]=1[C:9]1[NH:13][C:12](=[O:14])[N:11]([C:15]2[CH:32]=[CH:31][C:18]([C:19]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]([F:30])[F:29])[CH:23]=3)=[O:20])=[C:17]([O:33][CH3:34])[CH:16]=2)[N:10]=1

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 1366125144-(3-(5-(aminomethyl)-2-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-N-(3-(difluoromethyl)phenyl)-2-methoxybenzamide

Product 1

HCID 136245973HCID 136245973, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by following the procedure as described for step-2 of Intermediate-30 by using 4-(3-(5-(aminomethyl)-2-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-N-(3-(di flu oromethyl)phenyl)-2-methoxybenzamide (Intermediate-39, 0.050 g, 0.10 mmol), cyclopropane carbonyl chloride (0.016 g, 0.15 mmol), DIPEA (2.0 mL) and THF (2 mL) to afford 0.015 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 0.68 (d, J=8.7 Hz, 4H), 1.60 (m, 1H), 3.95 (s, 3H), 4.34 (d, J=5.4 Hz, 2H), 7.05 (m, 1H), 7.29 (d, J=7.9 Hz, 1H), 7.41-7.55 (m, 4H), 7.65 (d, J=9.0 Hz, 1H), 7.74 (s, 1H), 7.82 (d, J=8.7 Hz, 2H), 8.07 (s, 1H), 8.72 (m, 1H), 10.33 (s, 1H); MS (m/z): 566.29 (M−H)−.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-af425b61ba14478a952c537e9486f3f6
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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