Sodium Hydroxide → HCID 56597371, compound

HRID 409537Notes

Reaction equation

[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:8]=[C:9]([C:13]2[N:14]=[C:15]([C:22]([C:24]3[CH:25]=[CH:26][C:27]([NH:34][C:35](=[O:40])[NH:36][CH2:37][CH2:38][CH3:39])=[C:28]([CH:33]=3)[C:29]([O:31]C)=O)=[O:23])[N:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=23)[CH:10]=[CH:11][CH:12]=1)=[O:6]>CO>[O:40]=[C:35]1[N:36]([CH2:37][CH2:38][CH3:39])[C:29](=[O:31])[C:28]2[C:27](=[CH:26][CH:25]=[C:24]([C:22]([C:15]3[N:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]4=[C:13]([C:9]4[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=4)[C:5]([OH:4])=[O:6])[N:14]=3)=[O:23])[CH:33]=2)[NH:34]1

Participants

Conditions

Temperature: 70 °C

Procedure

1.31 ml (1.31 mmol) of a 1N aqueous solution of sodium hydroxide are added to 0.27 g (0.52 mmol) of methyl 5-({1-[3-(methoxycarbonyl)phenyl]imidazo[1,5-a]pyridin-3-yl}carbonyl)-2-[(propylcarbamoyl)amino]benzoate in 8 ml of methanol. The reaction medium is heated at 70° C. for 5.5 hours. The methanol is concentrated under reduced pressure. The residue is taken up in water. The aqueous phase is acidified with a 1N aqueous solution of hydrochloric acid, and then extracted with dichloromethane. The organic phase is dried over sodium sulphate, filtered, and then concentrated under reduced pressure. The solid obtained is taken up in methanol and then filtered, and dried at 50° C. under reduced pressure overnight. 0.245 g of a yellow solid is obtained.

Workup

concentrationThe methanol is concentrated under reduced pressure
extractionextracted with dichloromethane
dry with materialThe organic phase is dried over sodium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe solid obtained
filtrationfiltered
customdried at 50° C. under reduced pressure overnight

Sources & evidence

ORD record: ord-b8c593ffdc4d4861bcb91d1969780515
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759344B2

Reaction notes

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