Methanol → HCID 67300494, compound

HRID 1015450Notes

Reaction equation

HRID 1015450 reaction equation
[F:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([NH:18][CH:19]4[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20]4)=[O:17])=[CH:13][CH:14]=3)[C:9]([CH3:31])=[C:8]2[CH3:32])=[CH:4][CH:3]=1.[ClH:35].C(OCC)(=O)C.CO>C(OCC)(=O)C>[ClH:35].[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([NH:18][CH:19]4[CH2:23][CH2:22][NH:21][CH2:20]4)=[O:17])=[CH:13][CH:14]=3)[C:9]([CH3:31])=[C:8]2[CH3:32])=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 21866389Hydrogen chloride-ethyl acetateHCID 67300689HCID 67300689, compound

Product 1

HCID 67300494HCID 67300494, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 775 mg portion of tert-butyl 3-({[1-(4-fluorobenzyl)-2,3-dimethyl-1H-indol-5-yl]carbonyl}amino)pyrrolidine-1-carboxylate was dissolved in 3.2 ml of ethyl acetate, and 2.1 ml of 4 M hydrogen chloride/ethyl acetate was added, followed by stirring at room temperature for 15 minutes. Then, 2 ml of methanol was added, followed by overnight stirring at room temperature. The resulting solid was collected by filtration and washed with ethyl acetate/methanol (3/1) to obtain 479 mg of 1-(4-fluorobenzyl)-2,3-dimethyl-N-pyrrolidin-3-yl-1H-indole-5-carboxamide hydrochloride as a pale pink solid.

Workup

  1. waitfollowed by overnight
  2. stirringstirring at room temperature
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with ethyl acetate/methanol (3/1)

Sources & evidence

ORD record
ord-c134758b280f4bc9b9e482a97eed677e
Source dataset
uspto-grants-2011_07
Patent number
US07985764B2

Reaction notes

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