Diisopropylethylamine → HCID 66851674, compound

HRID 1466594Notes

Reaction equation

HRID 1466594 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[NH:12][N:11]=[C:10]([CH3:13])[C:9]=2[NH2:14])[CH:5]=[CH:6][CH:7]=1.[N:15]1[N:19]2[CH:20]=[CH:21][CH:22]=[N:23][C:18]2=[C:17]([C:24](O)=[O:25])[CH:16]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C1C=CN=CC=1.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([NH:14][C:24]([C:17]3[CH:16]=[N:15][N:19]4[CH:20]=[CH:21][CH:22]=[N:23][C:18]=34)=[O:25])=[C:10]([CH3:13])[NH:11][N:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1910189Pyrazolo[1,5-a]pyrimidine-3-carboxylic acidHCID 11038641((7-Azabenzotriazol-1-YL)oxy)tris(pyrrolidino)phosphonium hexafluorophosphateHCID 178434583HCID 178434583, compound

Product 1

HCID 66851674HCID 66851674, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5-(3-chlorophenyl)-3-methyl-1H-pyrazol-4-amine (113.3 mg, 0.546 mmol), pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (109.5 mg, 0.6712 mmol), 7-azabenzotriazol-1-yloxy-tris-(pyrrolidino)phosphonium hexafluorophosphate (338.2 mg, 0.652 mmol), N,N-diisopropylethylamine (0.30 mL, 1.7 mmol), and 4-dimethylaminopyridine (19.1 mg, 0.156 mmol) in 8.0 mL N,N-dimethylformamide was stirred at 50° C. for 15 hours. The reaction mixture was partitioned between ethyl acetate and water, and the organic portion washed with brine, dried over magnesium sulfate, and concentrated. The crude product was purified by reverse phase HPLC and lyophilized to give 86.9 mg (45%) of N-(3-(3-chlorophenyl)-5-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide. LCMS (ESI) m+H=353.0; 1H NMR (400 MHz, DMSO-d6) δ: 12.90 (s, 1H), 9.37 (d, J=7.0, 1H), 9.30 (s, 1H), 8.86 (dd, J=4.1, 1.3, 1H), 8.69 (s, 1H), 7.80 (d, J=12.1, 1H), 7.72 (d, J=7.6, 1H), 7.37 (t, J=7.8, 1H), 7.32 (dd, J=6.9, 4.4, 2H), 2.18 (s, 3H).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washthe organic portion washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-88f88a8da74d409aac9926221820b9f9
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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