Hydrogen chloride-ethyl acetate → HCID 67776798, compound

HRID 1026363Notes

Reaction equation

HRID 1026363 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[N:10]([N:12]=[C:13]([C:15]4[C:32]([F:33])=[CH:31][C:18]([O:19][CH2:20][C@@H:21]([NH:23]C(=O)OC(C)(C)C)[CH3:22])=[CH:17][C:16]=4[F:34])[CH:14]=3)[CH:11]=2)[CH2:3][CH2:2]1.[C:35](OCC)(=[O:37])[CH3:36].Cl>>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[N:10]([N:12]=[C:13]([C:15]4[C:16]([F:34])=[CH:17][C:18]([O:19][CH2:20][C@@H:21]([NH:23][C:35](=[O:37])[CH3:36])[CH3:22])=[CH:31][C:32]=4[F:33])[CH:14]=3)[CH:11]=2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86666331HCID 86666331, compound

Product 1

HCID 67776798HCID 67776798, compound

Procedure

A mixture of tert-butyl [(1S)-2-{4-[6-(cyclopropylmethoxy)pyrazolo[1,5-a]pyridin-2-yl]-3,5-difluorophenoxy}-1-methylethyl]carbamate (130 mg) and 4 M hydrogen chloride-ethyl acetate (2 mL) was stirred at room temperature for 30 min. The mixture was concentrated under reduced pressure. To the residue were added pyridine (2 mL) and acetic anhydride (0.26 mL). The mixture was stirred at room temperature for 30 min and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to afford the title compound (40 mg).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionTo the residue were added pyridine (2 mL) and acetic anhydride (0.26 mL)
  3. stirringThe mixture was stirred at room temperature for 30 min
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e890ee217f46427f884dec33ce9228dd
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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