Acetic Acid → HCID 86691715, compound

HRID 1426903Notes

Reaction equation

HRID 1426903 reaction equation
C[O:2][C:3]1[N:8]=[C:7]([C@H:9]2[CH2:13][CH2:12][CH2:11][N:10]2[C:14]2[CH:19]=[CH:18][N:17]3[N:20]=[CH:21][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:16]3[N:15]=2)[CH:6]=[CH:5][CH:4]=1.C(O)(=O)C.Br>CCOC(C)=O>[O:2]=[C:3]1[NH:8][C:7]([C@H:9]2[CH2:13][CH2:12][CH2:11][N:10]2[C:14]2[CH:19]=[CH:18][N:17]3[N:20]=[CH:21][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:16]3[N:15]=2)=[CH:6][CH:5]=[CH:4]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 86691716HCID 86691716, compound

Product 1

HCID 86691715HCID 86691715, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of (R)-ethyl 5-(2-(6-methoxypyridin-2-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (0.46 g, 1.25 mmol) and acetic acid (3.0 g, 50 mmol) was added HBr (3.1 g, 12.5 mmol, 33% in acetic acid). The reaction mixture was heated at 90° C. for 2 hours. After cooling, the reaction was diluted with EtOAc, washed with water, saturated NaHCO3, and brine, then dried (MgSO4), filtered, and concentrated. The crude material was purified by silica column chromatography, eluting with 4% MeOH/DCM to yield the desired product (0.3 g, 67% yield). MS (apci) m/z=354.1 (M+H).

Workup

  1. temperatureAfter cooling
  2. washwashed with water, saturated NaHCO3, and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by silica column chromatography
  7. washeluting with 4% MeOH/DCM

Sources & evidence

ORD record
ord-677b64fa2cee46ca9070b3ac208b4357
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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