Cyclopropanecarbonyl chloride → HCID 136245972, compound

HRID 59480Notes

Reaction equation

HRID 59480 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[NH:11][C:10]([C:14]3[CH:15]=[C:16]([CH:24]=[CH:25][C:26]=3[Cl:27])[CH2:17][NH:18][C:19]([CH:21]3[CH2:23][CH2:22]3)=[O:20])=[N:9]2)=[CH:4][C:3]=1[O:28][CH3:29].[CH:30]1([C:33](Cl)=[O:34])[CH2:32][CH2:31]1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:27][C:26]1[CH:25]=[CH:24][C:16]([CH2:17][NH:18][C:19]([CH:21]2[CH2:23][CH2:22]2)=[O:20])=[CH:15][C:14]=1[C:10]1[NH:11][C:12](=[O:13])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:33]([CH:30]3[CH2:32][CH2:31]3)=[O:34])=[C:3]([O:28][CH3:29])[CH:4]=2)[N:9]=1

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 136612554N-(3-(1-(4-amino-3-methoxyphenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-4-chlorobenzyl)cyclopropanecarboxamide

Product 1

HCID 136245972HCID 136245972, compoundYield 25.9%

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 N-(3-(1-(4-amino-3-methoxyphenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-4-chlorobenzyl)cyclopropanecarboxamide (Intermediate-37, 0.050 g, 0.120 mmol), cyclopropylcarbonyl chloride (0.018 g, 0.180 mmol), DIPEA (2.0 mL) and THF (5 mL) to afford 0.015 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 0.69 (s, 4H), 0.77 (s, 4H), 1.60 (m, 1H), 2.08 (m, 1H), 3.88 (s, 3H), 4.33 (d, J=5.4 Hz, 2H), 7.45 (m, 2H), 7.62 (s, 2H), 7.96 (d, J=8.4 Hz, 1H), 8.69 (m, 1H), 9.49 (s, 1H), 12.54 (s, 1H); MS (m/z): 482.10 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-b63017775e3c4030a185dafddcebbc04
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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