Isopropanol → HCID 66920706, compound

HRID 1365901Notes

Reaction equation

[NH2:1][C:2]1[C:7]([CH:8]=O)=[C:6]([NH:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[N:15]=[CH:14]3)[N:5]=[CH:4][N:3]=1.[CH3:28][NH:29][NH2:30].[CH3:31]C(O)C>O>[CH3:28][N:29]([CH3:31])[N:30]=[CH:8][C:7]1[C:6]([NH:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[N:15]=[CH:14]3)=[N:5][CH:4]=[N:3][C:2]=1[NH2:1]

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of crude 4-amino-6-[1-(3-fluoro-benzyl)-1H-indazol-5-ylamino]-pyrimidine-5-carbaldehyde (14.2 mg, 0.039 mmol) and methylhydrazine (5.4 mg, 0.118 mmol) in i-PrOH (1.5 mL) was stirred at 95° C. for 3 h, then diluted with water. The yellow precipitate was extracted with ethyl acetate (35 mL) and the organic extracts were evaporated. The residue was purified by flash column chromatography on silica gel (EtOAc then to 5% MeOH/EtOAc) to give the desired product (14.3 mg, 94%).

Workup

extractionThe yellow precipitate was extracted with ethyl acetate (35 mL)
customthe organic extracts were evaporated
customThe residue was purified by flash column chromatography on silica gel (EtOAc

Sources & evidence

ORD record: ord-9ee7824901d44d7bbeeaf3c95d2a8bd8
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893064B2

Reaction notes

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