Triethylamine → 1H-benzo[d][1,2,3]triazol-1-yl 2-amino-5-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

HRID 869114Notes

Reaction equation

C(N(CC)CC)C.[NH2:8][C:9]1[C:21]([C:22]([OH:24])=[O:23])=[C:12]2[N:13]=[C:14]([C:17]([F:20])([F:19])[F:18])[CH:15]=[CH:16][N:11]2[N:10]=1.CN(C(O[N:33]1[N:41]=[N:40][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)(Cl)Cl>[NH2:8][C:9]1[C:21]([C:22]([O:24][N:40]2[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[N:33]=[N:41]2)=[O:23])=[C:12]2[N:13]=[C:14]([C:17]([F:20])([F:18])[F:19])[CH:15]=[CH:16][N:11]2[N:10]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Triethylamine (994.9 mg, 1.370 mL, 9.832 mmol) was added to a suspension of 2-amino-5-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid 5a (2.2 g, 8.938 mmol) in chloroform (22 mL). TBTU (2.870 g, 8.938 mmol) was added to the solution and the reaction mixture was heated at 50° C. for 20 min, during which time a yellow precipitate formed. The reaction mixture was cooled to ambient temperature. The precipitate was isolated by filtration and washed with chloroform to leave the product (benzotriazol-1-yl 2-amino-5-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate) 6a as an off-white solid (2.8 g, 86% yield).). LC-MS (M+H)+ 364.0; 1H NMR (500 MHz, DMSO-d6) δ 9.40-9.28 (m, 1H), 8.19 (dt, J=8.5, 0.9 Hz, 1H), 7.80 (dt, J=8.4, 0.9 Hz, 1H), 7.72-7.63 (m, 2H), 7.55 (m, J=8.5, 6.9, 1.0 Hz, 1H), 7.13 (s, 2H).

Workup

customformed
temperatureThe reaction mixture was cooled to ambient temperature
customThe precipitate was isolated by filtration
washwashed with chloroform

Sources & evidence

ORD record: ord-5ab8bbf5f5f541c0914c2b73eaf173e5
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969360B2

Reaction notes

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