Tetrahydrofuran → (R)-ethyl 5-(2-(2-(3-aminopropoxy)-5-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

HRID 1426938Notes

Reaction equation

HRID 1426938 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[C@H:23]1[CH2:27][CH2:26][CH2:25][N:24]1[C:28]1[CH:33]=[CH:32][N:31]2[N:34]=[CH:35][C:36]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[C:30]2[N:29]=1.O.NN.C1COCC1>CO>[NH2:3][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[C@H:23]1[CH2:27][CH2:26][CH2:25][N:24]1[C:28]1[CH:33]=[CH:32][N:31]2[N:34]=[CH:35][C:36]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[C:30]2[N:29]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 86691731HCID 86691731, compound

Product 1

HCID 86691732(R)-ethyl 5-(2-(2-(3-aminopropoxy)-5-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylateYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-ethyl 5-(2-(2-(3-(1,3-dioxoisoindolin-2-yl)prop oxy)-5-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (200 mg, 0.359 mmol) and hydrazine monohydrate (115 mg, 3.59 mmol) were combined in MeOH (1 mL) and THF (1 mL) in a sealed vessel and heated at 60° C. for 20 minutes. After cooling to ambient temperature, the reaction was concentrated, followed by addition of NaOH (1 N, 2 mL). The mixture was extracted with DCM, and the combined organic extracts were dried (Na2SO4), filtered and concentrated to afford (R)-ethyl 5-(2-(2-(3-aminoprop oxy)-5-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (110 mg, 72% yield). MS (apci) m/z=428.2 (M+H).

Workup

  1. concentrationthe reaction was concentrated
  2. additionfollowed by addition of NaOH (1 N, 2 mL)
  3. extractionThe mixture was extracted with DCM
  4. dry with materialthe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-59c6ff070b57419d87e83b5493c21b0e
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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