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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 2278855
Notes
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Reaction equation

HRID 2278855 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 716216963-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-1,2,4-triazine-5,6-diamine

Product 1

HCID 71621698Methyl {5-amino-3-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-1,2,4-triazin-6-yl}carbamate

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent
2×

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

  1. filtrationThe precipitate was filtered off with suction
  2. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes