Methanol → 6-[4-(5-Cyclopropyl-2H-pyrazol-3-ylamino)-5-phenyl-pyrimidin-2-ylamino]-1,2-dihydro-indazol-3-one

HRID 855650Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[NH:10][N:11]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[CH:13]=2)[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][N:3]=1.C(OC([N:30]1[C:38]2[C:33](=[CH:34][CH:35]=[C:36]([NH2:39])[CH:37]=2)[C:32](=[O:40])[NH:31]1)=O)(C)(C)C.CO>C(O)CCC>[CH:14]1([C:12]2[CH:13]=[C:9]([NH:8][C:6]3[C:5]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:4][N:3]=[C:2]([NH:39][C:36]4[CH:37]=[C:38]5[C:33]([C:32](=[O:40])[NH:31][NH:30]5)=[CH:34][CH:35]=4)[N:7]=3)[NH:10][N:11]=2)[CH2:16][CH2:15]1

Participants

Conditions

Temperature: 95 °C

Procedure

To ((2-Chloro-5-phenyl-pyrimidin-4-yl)-(5-cyclopropyl-2H-pyrazol-3-yl)-amine (75 mg, 0.241 mmol), was added 6-Amino-3-oxo-2,3-dihydro-indazole-1-carboxylic acid tert-butyl ester (180 mg, 0.72 mmol) in n-butanol and the solution was heated to 95° C. in a sealed tube. After 12 hr, the solution was concentrated and the title compound was isolated by preparative HPLC as a white solid (5.2 mg, 5% yield) HNMR (500 MHz, MeOH d-6). □17.82–7.80 (2H, m), 7.59–7.50 (6H, m), 7.19–7.17 (1H, m), 6.08 (1H, s), 2.65 (1H, m), 0.91–0.89 (2H, m), 0.45 (2H, m); LCMS m/e: 1.9 min, 425.1 (M+H), 423.1 (M−H).

Workup

concentrationthe solution was concentrated

Sources & evidence

ORD record: ord-9f628db4248345c881bceb093cde626c
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262200B2

Reaction notes

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