Benzotriazol-1-yl 2-amino-6-fluoro-pyrazolo[1,5-a]pyrimidine-3-carboxylate → (R)-2-amino-6-fluoro-N-(4-((1-methylpiperidin-3-yl)oxy)pyrimidin-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 1850679Notes

Reaction equation

HRID 1850679 reaction equation
[NH2:1][C:2]1[C:11]([C:12]([O:14]N2C3C=CC=CC=3N=N2)=O)=[C:5]2[N:6]=[CH:7][C:8]([F:10])=[CH:9][N:4]2[N:3]=1.[CH3:24][N:25]1[CH2:30][CH2:29][CH2:28][C@@H:27]([O:31][C:32]2[C:37]([NH2:38])=[CH:36][N:35]=[CH:34][N:33]=2)[CH2:26]1>CN1C(=O)CCC1>[NH2:1][C:2]1[C:11]([C:12]([NH:38][C:37]2[C:32]([O:31][C@@H:27]3[CH2:28][CH2:29][CH2:30][N:25]([CH3:24])[CH2:26]3)=[N:33][CH:34]=[N:35][CH:36]=2)=[O:14])=[C:5]2[N:6]=[CH:7][C:8]([F:10])=[CH:9][N:4]2[N:3]=1

Participants

4

Reactant 2

HCID 86720894Benzotriazol-1-yl 2-amino-6-fluoro-pyrazolo[1,5-a]pyrimidine-3-carboxylateHCID 90411653(R)-4((1-methylpiperidin-3-yl)oxy)pyrimidin-5-amine

Product 1

HCID 85473432(R)-2-amino-6-fluoro-N-(4-((1-methylpiperidin-3-yl)oxy)pyrimidin-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of benzotriazol-1-yl 2-amino-6-fluoro-pyrazolo[1,5-a]pyrimidine-3-carboxylate 6a (125 mg, 0.3990 mmol) and 4-[[(3R)-1-methyl-3-piperidyl]oxy]pyrimidin-5-amine 7a (83.10 mg, 0.3990 mmol) in NMP (2 mL) was heated at 100° C. overnight. The reaction mixture was cooled to RT, passed through a SCX cartridge, eluting with 2M ammonia in methanol. The product fractions were combined, concentrated in vacuo and purified by HPLC. The title product I-A-1 was isolated (60 mg., 38.9%)

Workup

  1. washeluting with 2M ammonia in methanol
  2. concentrationconcentrated in vacuo
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-155203ab24834119b023578ec8550e1d
Source dataset
uspto-grants-2015_02
Patent number
US08957078B2

Reaction notes

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