Methyl chloroformate → Methyl {5-amino-3-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-1,2,4-triazin-6-yl}carbamate

HRID 2278855Notes

Reaction equation

[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:15]=[N:16][C:17]([NH2:21])=[C:18]([NH2:20])[N:19]=2)=[N:6]1.Cl[C:27]([O:29][CH3:30])=[O:28].C(N(CC)CC)C>ClCCl>[NH2:20][C:18]1[N:19]=[C:14]([C:7]2[C:8]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[N:5]([CH2:4][C:3]3[CH:22]=[CH:23][CH:24]=[CH:25][C:2]=3[F:1])[N:6]=2)[N:15]=[N:16][C:17]=1[NH:21][C:27](=[O:28])[O:29][CH3:30]

Participants

Conditions

Temperature: 0 °C

Procedure

200 mg (purity 67%, 0.398 mmol) of 3-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-1,2,4-triazine-5,6-diamine were admixed with 4 ml of dichloromethane and cooled to 0° C. 151 mg (1.594 mmol) of methyl chloroformate dissolved in 1 ml of dichloromethane and 161 mg (1.594 mmol) of triethylamine were added and the mixture was stirred at RT for 15 min. The precipitate was filtered off with suction and dried under high vacuum. This gave 97 mg (61% of theory) of the target compound.

Workup

filtrationThe precipitate was filtered off with suction
customdried under high vacuum

Sources & evidence

ORD record: ord-3297eab5479e4d35b81a04a6f51304b1
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133191B2

Reaction notes

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