4-chloro-1-methyl-1H-pyrazole-5-carboxylic acid → HCID 51034816, compound

HRID 2382722Notes

Reaction equation

HRID 2382722 reaction equation
F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[Cl:23][C:24]1[CH:28]=[N:27][N:26]([CH3:29])[C:25]=1[C:30]([OH:32])=O.[C:33]1([C:39]2[N:40]=[C:41]3[CH:46]=[C:45]([NH2:47])[CH:44]=[CH:43][N:42]3[CH:48]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C=O)C.C(OCC)(=O)C>[C:33]1([C:39]2[N:40]=[C:41]3[CH:46]=[C:45]([NH:47][C:30]([C:25]4[N:26]([CH3:29])[N:27]=[CH:28][C:24]=4[Cl:23])=[O:32])[CH:44]=[CH:43][N:42]3[CH:48]=2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 3

HCID 6708234-chloro-1-methyl-1H-pyrazole-5-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 569555022-Phenylimidazo[1,2-a]pyridin-7-amine

Product 1

HCID 51034816HCID 51034816, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under an atmosphere of nitrogen, N—N-diisopropylethylamine (749 mg, 6 mmol) and 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU, 744 mg, 1.94 mmol) were added to a solution of 4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid (310 mg, 1.94 mmol, Art-Chem B000148) in DMF (5 ml). After 30 min, 2-phenyl-imidazo[1,2-a]pyridin-7-ylamine (404 mg, 1.94 mmol) was added, and the brown solution was stirred over the weekend (r.t.). The reaction mixture was taken up in ethyl acetate and washed with water. After drying (Na2SO4), the solvent was evaporated and the title compound (170 mg, 25%) was isolated by column chromatography (silica gel, heptane:ethyl acetate=100:0-50:50). MS (m/e)=352.2 [M+H+].

Workup

  1. washwashed with water
  2. dry with materialAfter drying (Na2SO4)
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-5c1c63ac51354932a1091a8f871d5503
Source dataset
uspto-grants-2012_09
Patent number
US08263584B2

Reaction notes

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