Phosgene → HCID 68490203, compound

HRID 1822476Notes

Reaction equation

HRID 1822476 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:21]=3)[CH2:16][NH:15]2)=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2].[C:38](Cl)(Cl)=[O:39].Cl.[CH2:43]([NH2:49])[CH2:44]CCC=C>>[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:21]=3)[CH2:16][N:15]2[C:38](=[O:39])[NH:49][CH2:43][CH3:44])=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 6371PhosgeneHCID 207653161-{[4-(7-Methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl esterHCID 77230248HCID 77230248, compound

Product 1

HCID 68490203HCID 68490203, compoundYield 86.8%

Procedure

Reaction of compound 12 (330 mg, 0.66 mmol), phosgene (1.6 ml, 1.9 M in toluene, 3 mmol) and hex-5-enylamine hydrochloride (500 mg, 3.68 mmol) following the procedure described in Example 120 gave the pure title product (328 mg, 80%), MS (M+H+) 627.

Sources & evidence

ORD record
ord-aa20b0079f32415dae24dc66ed2e5ff9
Source dataset
uspto-grants-2009_10
Patent number
US07608590B2

Reaction notes

Loading…