Diisopropylethylamine → HCID 178522411, compound

HRID 1466571Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]([NH2:13])=[CH:11][NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[N:14]1[N:18]2[CH:19]=[CH:20][CH:21]=[N:22][C:17]2=[C:16]([C:23](O)=[O:24])[CH:15]=1.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:12]([NH:13][C:23]([C:16]3[CH:15]=[N:14][N:18]4[CH:19]=[CH:20][CH:21]=[N:22][C:17]=34)=[O:24])=[CH:11][NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 3-(3-chlorophenyl)-1H-pyrazol-4-amine (95.3 mg, 0.492 mmol, 1 eq), pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (90.6 mg, 0.555 mmol, 1.13 eq), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uranium hexafluorophosphate (247.3 mg, 0.6504 mmol, 1.32 eq), N,N-diisopropylethylamine (0.20 mL, 1.1 mmol, 2.3 eq), and 4-dimethylaminopyridine (24.1 mg, 0.197 mmol, 0.40 eq) in 5.0 mL N,N-dimethylformamide was stirred at 50° C. for 3 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 33.8 mg (20%) of N-(3-(3-chlorophenyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide. LCMS (ESI) m+H=339.0; 1H NMR (400 MHz, DMSO-d6) δ: 13.05 (s, 1H), 9.99 (s, 1H), 9.38 (d, 1H), 8.84 (d, 1H), 8.70 (s, 1H), 8.31 (s, 1H), 7.86 (s, 1H), 7.78 (d, 1H), 7.58 (t, 1H), 7.50 (d, 1H), 7.34 (d of d, 1H).

Workup

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

Sources & evidence

ORD record: ord-af8f0053b913476da731d11beb267d84
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999998B2

Reaction notes

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