HCID 66650273, compound → 5-{5-[5-(4-Chloro-3-methyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidin-3-yl]-[1,2,4]oxadiazol-3-yl}-pyridin-2-ylamine

HRID 418237Notes

Reaction equation

HRID 418237 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]3[N:18]=[CH:19][C:20]([C:21](O)=[O:22])=[C:10]3[N:9]=2)=[CH:4][C:3]=1[CH3:24].[NH2:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([NH:32]O)=[NH:31])=[CH:28][N:27]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([F:16])([F:17])[F:15])[N:11]3[N:18]=[CH:19][C:20]([C:21]4[O:22][N:32]=[C:30]([C:29]5[CH:34]=[CH:35][C:26]([NH2:25])=[N:27][CH:28]=5)[N:31]=4)=[C:10]3[N:9]=2)=[CH:4][C:3]=1[CH3:24]

Participants

3

Reactant 2

HCID 66650273HCID 66650273, compoundHCID 178513347HCID 178513347, compound

Product 1

HCID 160677035-{5-[5-(4-Chloro-3-methyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidin-3-yl]-[1,2,4]oxadiazol-3-yl}-pyridin-2-ylamine

Procedure

The title compound was prepared from 5-(4-chloro-3-methyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.6) (178 mg, 0.5 mmol) and 6-amino-N-hydroxy-nicotinamidine (example B.4) (114 mg, 0.75 mmol) according to general procedure II. Obtained after flash chromatography on silica gel (ethyl acetate/heptane) and further purification by crystallization (dichloromethane/hexane) as a yellow solid (66 mg, 28%). MS (ISP) 471.9 [(M+H)+]; mp 262° C.

Workup

  1. customObtained after flash chromatography
  2. customon silica gel (ethyl acetate/heptane) and further purification
  3. customby crystallization (dichloromethane/hexane) as a yellow solid (66 mg, 28%)

Sources & evidence

ORD record
ord-ed36ed2ba5bf478dae27ed23a321f86a
Source dataset
uspto-grants-2012_01
Patent number
US08093263B2

Reaction notes

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