4-chloro-1-methyl-1H-pyrazole-5-carboxylic acid → HCID 51035029, compound

HRID 2382735Notes

Reaction equation

HRID 2382735 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.[N:33]1([C:39]2[N:44]3[CH:45]=[C:46]([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[N:47]=[C:43]3[CH:42]=[C:41]([NH2:54])[N:40]=2)[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>CN(C=O)C.C(OCC)(=O)C>[N:33]1([C:39]2[N:44]3[CH:45]=[C:46]([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[N:47]=[C:43]3[CH:42]=[C:41]([NH:54][C:30]([C:25]3[N:26]([CH3:29])[N:27]=[CH:28][C:24]=3[Cl:23])=[O:32])[N:40]=2)[CH2:38][CH2:37][O:36][CH2:35][CH2:34]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 670419775-Morpholin-4-yl-2-phenyl-imidazo[1,2-c]pyrimidin-7-ylamine

Product 1

HCID 51035029HCID 51035029, compoundYield 1.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under an atmosphere of nitrogen, N—N-diisopropylethylamine (121 mg) and 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU, 120 mg) were added to a solution of 4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid (50 mg, 0.31 mmol, Art-Chem B000148) in DMF (3 ml). After 30 min, 5-morpholin-4-yl-2-phenyl-imidazo[1,2-c]pyrimidin-7-ylamine (110 mg, 0.37 mmol) was added, and the black solution was stirred at r.t. overnight. The reaction mixture was taken up in ethyl acetate and washed with water. After drying (Na2SO4), the solvent was evaporated and the title compound (2 mg, 1.1%) was isolated by preparative, inverse-phase HPLC (Agilent Zorbax XdB-C18 column, time per run ˜7 min, flow rate 30 ml/min, solvent gradient H2O/CH3CN=95:5-5:95). MS (m/e)=438.2 [M+H+].

Workup

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

Sources & evidence

ORD record
ord-c7be7f5e5af44db49859392eed766748
Source dataset
uspto-grants-2012_09
Patent number
US08263584B2

Reaction notes

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