Ammonia → HCID 86680812, compound

HRID 589851Notes

Reaction equation

C(OC([NH:8][CH2:9][CH2:10][N:11]1[C:15]([Cl:16])=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[N:24])[CH:18]=2)[C:13]([C:25]([O:27][CH3:28])=[O:26])=[CH:12]1)=O)(C)(C)C.Cl.O.N>CO>[NH2:8][CH2:9][CH2:10][N:11]1[C:15]([Cl:16])=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[N:24])[CH:18]=2)[C:13]([C:25]([O:27][CH3:28])=[O:26])=[CH:12]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 13.5 g (33.4 mmol) of methyl 1-(2-tert-butyloxycarbonylaminoethyl)-5-chloro-4-(3-cyanophenyl)-1H-pyrrole-3-carboxylate in 50 ml of methanol are added 80 ml (320 mmol) of 4N hydrochloric acid and the mixture is heated vigorously at 60° C. for 2 hours. 150 ml of water are then added and the solution is basified by adding aqueous ammonia. The product is extracted with dichloromethane, the organic phase is then dried over sodium sulfate and the solvent is evaporated off under reduced pressure to give a yellow oil, which is purified by chromatography on a column of 80 g of silica gel, eluting with a mixture of 0.3% aqueous ammonia and 3% methanol in dichloromethane, to give 8.4 g of methyl 1-(2-aminoethyl)-5-chloro-4-(3-cyanophenyl)-1H-pyrrole-3-carboxylate in the form of a white powder after crystallizing, triturating in diisopropyl ether, filtering off and drying.

Workup

extractionThe product is extracted with dichloromethane
dry with materialthe organic phase is then dried over sodium sulfate
customthe solvent is evaporated off under reduced pressure
customto give a yellow oil, which
customis purified by chromatography on a column of 80 g of silica gel
washeluting with a mixture of 0.3% aqueous ammonia and 3% methanol in dichloromethane

Sources & evidence

ORD record: ord-0ce682d4451a47bfa089d7a0a2f8a7b4
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233965B2

Reaction notes

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