Isopropanol → HCID 67471102, compound

HRID 1426940Notes

Reaction equation

HRID 1426940 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([C@H:10]2[CH2:14][CH2:13][CH2:12][NH:11]2)[CH:4]=1.CCN(C(C)C)C(C)C.Cl[C:25]1[CH:30]=[CH:29][N:28]2[N:31]=[CH:32][CH:33]=[C:27]2[N:26]=1.C(O)(C)C>CCOCC>[F:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:25]2[CH:30]=[CH:29][N:28]3[N:31]=[CH:32][CH:33]=[C:27]3[N:26]=2)[CH:4]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 81531DiisopropylethylamineHCID 210717595-Chloropyrazolo(1,5-a)pyrimidineHCID 66847770HCID 66847770, compound

Product 1

HCID 67471102HCID 67471102, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of (R)-4-fluoro-2-(pyrrolidin-2-yl)phenol hydrochloride (Example 20, Step B, 1.50 g, 6.89 mmol), DIEA (2.67 g, 20.7 mmol), 5-chloropyrazolo[1,5-a]pyrimidine (1.11 g, 7.24 mmol) and isopropanol (1 mL) was heated at 120° C. overnight. The reaction was poured into ether (50 mL) and extracted with NaOH (1N aqueous, 3×25 mL). The combined aqueous extracts were brought to pH 4 with concentrated HCl and extracted with DCM. The combined DCM extracts were filtered through phase separator paper and concentrated to provide (R)-4-fluoro-2-(1-(pyrazolo[1,5-a]pyrimidin-5-yl)pyrrolidin-2-yl)phenol (1.82 g, 89% yield) as beige solid. MS (apci) m/z=299.4 (M+H).

Workup

  1. extractionextracted with NaOH (1N aqueous, 3×25 mL)
  2. extractionextracted with DCM
  3. filtrationThe combined DCM extracts were filtered through phase
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-55a07783d55c4257a1e0ef71191b374a
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

Loading…