HCID 86720889, compound → 2-amino-6-fluoro-N-(3-methyl-4-(pyrrolidin-1-yl)isothiazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 1850704Notes

Reaction equation

[NH2:1][C:2]1[C:11]([C:12]([O:14]N2C3C=C(Cl)C=CC=3N=N2)=O)=[C:5]2[N:6]=[CH:7][C:8]([F:10])=[CH:9][N:4]2[N:3]=1.[CH3:25][C:26]1[C:30]([N:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)=[C:29]([NH2:36])[S:28][N:27]=1>N1C=CC=CC=1>[NH2:1][C:2]1[C:11]([C:12]([NH:36][C:29]2[S:28][N:27]=[C:26]([CH3:25])[C:30]=2[N:31]2[CH2:32][CH2:33][CH2:34][CH2:35]2)=[O:14])=[C:5]2[N:6]=[CH:7][C:8]([F:10])=[CH:9][N:4]2[N:3]=1

Participants

Conditions

Temperature: 105 °C

Procedure

A mixture of (6-chlorobenzotriazol-1-yl) 2-amino-6-fluoro-pyrazolo[1,5-a]pyrimidine-3-carboxylate (140.4 mg, 0.4038 mmol), 3-methyl-4-(pyrrolidin-1-yl)isothiazol-5-amine (37 mg, 0.2019 mmol) (synthesized according to preparation 13) in pyridine (3 mL) was heated at 105° C. for 24 h. The mixture was concentrated in vacuo and the residue was purified by fractionlynx. The clean fractions were combined and freeze dried to yield 2-amino-6-fluoro-N-(3-methyl-4-(pyrrolidin-1-yl)isothiazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide as a pale yellow solid. (25 mg, 26%). MS (ES+) 362.1.

Workup

concentrationThe mixture was concentrated in vacuo
customthe residue was purified by fractionlynx
customfreeze dried

Sources & evidence

ORD record: ord-6f6b886918374738a74307029b18fe69
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957078B2

Reaction notes

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