Propylamine → HCID 66653425, compound

HRID 409536Notes

Reaction equation

ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[CH:23]=[CH:22][C:21]([C:24]([C:26]2[N:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]3=[C:28]([C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([O:43][CH3:44])=[O:42])[CH:36]=3)[N:27]=2)=[O:25])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17].[CH2:45]([NH2:48])[CH2:46][CH3:47].C(N(CC)CC)C>O1CCOCC1.O>[CH3:44][O:43][C:41]([C:37]1[CH:36]=[C:35]([C:28]2[N:27]=[C:26]([C:24]([C:21]3[CH:22]=[CH:23][C:14]([NH:13][C:5](=[O:11])[NH:48][CH2:45][CH2:46][CH3:47])=[C:15]([CH:20]=3)[C:16]([O:18][CH3:19])=[O:17])=[O:25])[N:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=23)[CH:40]=[CH:39][CH:38]=1)=[O:42]

Participants

Conditions

Temperature: 100 °C

Procedure

0.181 g (0.61 mmol) of triphosgene is added, under an inert atmosphere, to 0.75 g (0.87 mmol) of methyl 2-amino-5-({1-[3-(methoxycarbonyl)phenyl]imidazo[1,5-a]pyridin-3-yl}carbonyl)benzoate in 10 ml of dioxane. The reaction medium is heated at 100° C. for 3 hours. 0.14 ml (1.75 mmol) of propylamine and 0.37 ml (2.62 mmol) of triethylamine are added at ambient temperature. After stirring for 2 hours at ambient temperature, the reaction medium is hydrolysed with water. The medium is filtered, washed with water, and dried under reduced pressure at 50° C. overnight. The solid obtained is purified by silica gel column chromatography with a dichloromethane/methanol (95/5) mixture. 0.27 g of a yellow powder is obtained.

Workup

filtrationThe medium is filtered
washwashed with water
customdried under reduced pressure at 50° C. overnight
customThe solid obtained
customis purified by silica gel column chromatography with a dichloromethane/methanol (95/5) mixture

Sources & evidence

ORD record: ord-90a2daac2ff54e3c965a2b5f5927cdef
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759344B2

Reaction notes

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