Hydrochloric Acid → HCID 89444490, compound

HRID 574643Notes

Reaction equation

HRID 574643 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][C@@H:5]([OH:31])[C@@H:6]2[N:12]1[C:20]2[CH2:19][CH2:18][N:17](C(C)C)[CH2:16][C:15]=2[C:14]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[N:13]1.Cl>C(O)C>[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][C@@H:5]([OH:31])[C@@H:6]2[N:12]1[C:20]2[CH2:19][CH2:18][NH:17][CH2:16][C:15]=2[C:14]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[N:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71516117HCID 71516117, compound

Product 1

HCID 89444490HCID 89444490, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

According to Scheme 8: A mixture of (1R,2R)-4,6-difluoro-1-[3-(4-fluoro-phenyl)-5-isopropyl-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1-yl]-indan-2-ol (11ae) (0.2 g, 0.468 mmol), ethanol (14 ml) and 2N aqueous HCl (14 ml) was stirred at 80° C. for 6h. The mixture was concentrated in vacuo. After addition of aqueous saturated NaHCO3, the mixture was extracted 3 times with ethyl acetate, solvents were evaporated in vacuo and the residue freeze-dried from CH3CN-water to give 0.170 g of (1R,2R)-4,6-difluoro-1-[3-(4-fluoro-phenyl)-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1-yl]-indan-2-ol (13a).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionAfter addition of aqueous saturated NaHCO3
  3. extractionthe mixture was extracted 3 times with ethyl acetate, solvents
  4. customwere evaporated in vacuo
  5. dry with materialthe residue freeze-dried from CH3CN-water

Sources & evidence

ORD record
ord-1bedcb40821d424ab5ba997e5727e96c
Source dataset
uspto-grants-2015_05
Patent number
US09034897B2

Reaction notes

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