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Heptane → Tak-272

HRID 1260118
Notes
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Reaction equation

HRID 1260118 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[C:16]([N:18]([CH2:33][CH:34]([CH3:36])[CH3:35])[C@H:19]1[CH2:24][C@@H:23]([C:25]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[O:26])[CH2:22][NH:21][CH2:20]1)=[O:17].C(OCC)(=O)C.[ClH:43].CCCCCCC>C(OCC)(=O)C>[ClH:43].[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[C:16]([N:18]([CH2:33][CH:34]([CH3:36])[CH3:35])[C@H:19]1[CH2:24][C@@H:23]([C:25]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[O:26])[CH2:22][NH:21][CH2:20]1)=[O:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8900Heptane2×HCID 21866389Hydrogen chloride-ethyl acetateHCID 44554894Imarikiren

Product 1

HCID 56591871Tak-272

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

1-(4-Methoxybutyl)-N-(2-methylpropyl)-N-[(3S,5R)-5-(morpholin-4-ylcarbonyl)piperidin-3-yl]-1H-benzimidazole-2-carboxamide (24.4 g) was dissolved in ethyl acetate (225 ml), and the mixture was heated to 45-55° C. 4M Hydrogen chloride-ethyl acetate (12.8 ml) was added dropwise, and the precipitate was dissolved at the same temperature. After confirmation of dissolution, heptane (75 ml) was added dropwise, and the mixture was cooled to 25-35° C. The seed crystal (45 mg) was added and the mixture was stirred for 30 min. The mixture was heated to 50-55° C., and heptane (150 ml) was added dropwise. The mixture was stirred at the same temperature for 1 hr, gradually cooled to 0-5° C., and stirred at the same temperature for 1 hr. The precipitated crystals were collected by filtration, washed with ethyl acetate-heptane (90 ml), and dried under reduced pressure at 40-50° C. to give the object product (15.3 g).

Workup

  1. dissolutionthe precipitate was dissolved at the same temperature
  2. additionwas added dropwise
  3. temperaturethe mixture was cooled to 25-35° C
  4. temperatureThe mixture was heated to 50-55° C.
  5. stirringThe mixture was stirred at the same temperature for 1 hr
  6. temperaturegradually cooled to 0-5° C.
  7. stirringstirred at the same temperature for 1 hr
  8. filtrationThe precipitated crystals were collected by filtration
  9. washwashed with ethyl acetate-heptane (90 ml)
  10. customdried under reduced pressure at 40-50° C.

Sources & evidence

ORD record
ord-665ce3100b2b4a2f8d20a05728687da0
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08466282B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes