Hydrazine → HCID 49857039, compound

HRID 1466589Notes

Reaction equation

HRID 1466589 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:38][CH3:39])=[C:6]([C:8]2[C:12]([NH:13][C:14]([C:16]3[CH:17]=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[O:15])=[CH:11][N:10]([CH2:25][CH2:26][N:27]3C(=O)C4C(=CC=CC=4)C3=O)[N:9]=2)[CH:7]=1.NN>C(O)C>[NH2:27][CH2:26][CH2:25][N:10]1[CH:11]=[C:12]([NH:13][C:14]([C:16]2[CH:17]=[N:18][N:19]3[CH:24]=[CH:23][CH:22]=[N:21][C:20]=23)=[O:15])[C:8]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:38][CH3:39])=[N:9]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 66851233HCID 66851233, compound

Product 1

HCID 49857039HCID 49857039, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-(3-(5-chloro-2-methoxyphenyl)-1-(2-(1,3-dioxoisoindolin-2-yl)ethyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (prepared following the synthetic procedures described for Example 14) (104.1 mg, 0.192 mmol) in 8 mL ethanol was added hydrazine (78 μL, 2.5 mmol). The reaction mixture was stirred at room temperature for 18 hours, and then concentrated. The crude product was purified by reverse phase HPLC and lyophilized to give 17.7 mg (15.4%) of N-(1-(2-aminoethyl)-3-(5-chloro-2-methoxyphenyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide. LCMS (ESI) m+H=412.1; 1H NMR (400 MHz, DMSO-d6) δ: 9.68 (s, 1H), 9.33 (dd, J=7.0, 1.6, 1H), 8.77 (dd, J=4.2, 1.6, 1H), 8.65 (s, 1H), 8.30 (s, 1H), 7.49 (dd, J=8.8, 2.7, 1H), 7.42 (d, J=2.7, 1H), 7.29 (m, 2H), 4.14 (t, J=6.2, 2H), 3.85 (s, 3H), 2.99 (t, J=6.2, 2H).

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-635ae5d823d544f483a2c4ea95c5227e
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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