Hydrazine hydrate (1:1) → HCID 86691718, compound

HRID 1426905Notes

Reaction equation

HRID 1426905 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][CH2:14][O:15][C:16]1[N:21]=[C:20]([C@H:22]2[CH2:26][CH2:25][CH2:24][N:23]2[C:27]2[CH:32]=[CH:31][N:30]3[N:33]=[CH:34][C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:29]3[N:28]=2)[CH:19]=[CH:18][CH:17]=1.CO.C1COCC1.NN.O>O>[NH2:3][CH2:12][CH2:13][CH2:14][O:15][C:16]1[N:21]=[C:20]([C@H:22]2[CH2:26][CH2:25][CH2:24][N:23]2[C:27]2[CH:32]=[CH:31][N:30]3[N:33]=[CH:34][C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:29]3[N:28]=2)[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 21899815MeOH tetrahydrofuranHCID 86691717HCID 86691717, compound

Product 1

HCID 86691718HCID 86691718, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (R)-ethyl 5-(2-(6-(3-(1,3-dioxoisoindolin-2-yl)prop oxy)pyridin-2-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (0.11 g, 0.20 mmol) in 1:1 MeOH/THF (12 mL) was added hydrazine-H2O (0.10 g, 2.0 mmol). The reaction mixture was heated at 50° C. for 24 hours. After cooling, the reaction mixture was poured into water then extracted with DCM (3×20 mL). The combined organics were dried (MgSO4), filtered, and concentrated to afford the desired product (70 mg, 84% yield). MS (apci) m/z=441.1 (M+H).

Workup

  1. temperatureAfter cooling
  2. extractionthen extracted with DCM (3×20 mL)
  3. dry with materialThe combined organics were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f6e361ceb7564ed08071883190b33b8b
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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