Hydrochloric Acid → HCID 67471093, compound

HRID 1426906Notes

Reaction equation

HRID 1426906 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[N:11]=[C:10]([C@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17]2[CH:22]=[CH:21][N:20]3[N:23]=[CH:24][C:25]([C:26]([O:28]CC)=[O:27])=[C:19]3[N:18]=2)[CH:9]=[CH:8][CH:7]=1.C1COCC1.CO.[Li+].[OH-].Cl>CO>[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[N:11]=[C:10]([C@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17]2[CH:22]=[CH:21][N:20]3[N:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[C:19]3[N:18]=2)[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 86691718HCID 86691718, compound

Product 1

HCID 67471093HCID 67471093, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (R)-ethyl 5-(2-(6-(3-aminopropoxy)pyridin-2-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (70 mg, 0.17 mmol) in 3:1 THF/MeOH (8 mL) was added LiOH (1 N, 1.5 mL, 1.5 mmol) and the reaction mixture was heated at 70° C. for 20 hours. After cooling, the reaction mixture was diluted with MeOH, acidified with 1 N HCl (1.5 mL), and concentrated to afford the desired product (65 mg, 100% yield). MS (apci) m/z=383.1 (M+H).

Workup

  1. temperatureAfter cooling
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-c96023c565e24537aef025fd301165b1
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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