Hydrochloric Acid → 1-[2-Fluoro-4-(2-{[4-(4-methylpiperazin-1-yl)piperidine-1-carbonyl]amino}piperidin-4-yloxy)phenylcarbamoyl]cyclopropanecarboxylic acid benzyl ester trihydrochloride

HRID 388500Notes

Reaction equation

HRID 388500 reaction equation
[CH2:1]([O:8][C:9]([C:11]1([C:14](=[O:46])[NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH:23]3[CH2:28][CH2:27][NH:26][CH:25]([NH:29][C:30]([N:32]4[CH2:37][CH2:36][CH:35]([N:38]5[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]5)[CH2:34][CH2:33]4)=[O:31])[CH2:24]3)=[CH:18][C:17]=2[F:45])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:47]>C(OCC)(=O)C>[ClH:47].[ClH:47].[ClH:47].[CH2:1]([O:8][C:9]([C:11]1([C:14](=[O:46])[NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH:23]3[CH2:28][CH2:27][NH:26][CH:25]([NH:29][C:30]([N:32]4[CH2:37][CH2:36][CH:35]([N:38]5[CH2:39][CH2:40][N:41]([CH3:44])[CH2:42][CH2:43]5)[CH2:34][CH2:33]4)=[O:31])[CH2:24]3)=[CH:18][C:17]=2[F:45])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68496027HCID 68496027, compound

Product 1

HCID 684981621-[2-Fluoro-4-(2-{[4-(4-methylpiperazin-1-yl)piperidine-1-carbonyl]amino}piperidin-4-yloxy)phenylcarbamoyl]cyclopropanecarboxylic acid benzyl ester trihydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

1-[2-Fluoro-4-(2-{[4-(4-methylpiperazin-1-yl)piperidine-1-carbonyl]amino}piperidin-4-yloxy)phenylcarbamoyl]cyclopropanecarboxylic acid benzyl ester (189 mg) was dissolved in ethyl acetate (6 ml), and 4N hydrochloric acid in ethyl acetate (0.3 ml) was added. The resultant mixture was concentrated under reduced pressure, and methanol (0.5 ml) and ethyl acetate (4 ml) was added. The precipitate obtained by filtration was hygroscopic, thus it was collected using methanol (10 ml). The collected solution was again concentrated under reduced pressure, and methanol (0.5 ml) and tert-butyl methyl ether (4 ml) was added. The precipitate was filtered to give the title compound (102 mg).

Workup

  1. concentrationThe resultant mixture was concentrated under reduced pressure, and methanol (0.5 ml) and ethyl acetate (4 ml)
  2. additionwas added
  3. customThe precipitate obtained by filtration
  4. customthus it was collected
  5. concentrationThe collected solution was again concentrated under reduced pressure, and methanol (0.5 ml) and tert-butyl methyl ether (4 ml)
  6. additionwas added
  7. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-d1eba45d81564209a7059e2cdfb763b8
Source dataset
uspto-grants-2013_02
Patent number
US08377938B2

Reaction notes

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