Ethyl chloroformate → Ethyl {4,6-diamino-2-[6-fluoro-3-(2-fluorobenzyl)-1H-pyrazolo [4,3-b]pyridin-1-yl]pyrimidin-5-yl}carbamate

HRID 626616Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[N:10]([C:11]3[N:16]=[C:15]([NH2:17])[C:14]([NH2:18])=[C:13]([NH2:19])[N:12]=3)[N:9]=[C:8]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[C:5]2=[N:6][CH:7]=1.Cl[C:29]([O:31][CH2:32][CH3:33])=[O:30]>N1C=CC=CC=1>[NH2:19][C:13]1[C:14]([NH:18][C:29](=[O:30])[O:31][CH2:32][CH3:33])=[C:15]([NH2:17])[N:16]=[C:11]([N:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([F:1])[CH:3]=3)[C:8]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])=[N:9]2)[N:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Under argon, 300 mg (0.814 mmol) of the compound from example 6A were initially charged in pyridine (10 ml), the mixture was cooled to 0° C. and 78 μl (0.814 mmol) of ethyl chloroformate were then added dropwise. The reaction mixture was stirred at 0° C. for 1 h and then concentrated. The residue was separated by means of preparative RP-HPLC (acetonitrile:water (+0.1% formic acid)−gradient) and the product fractions were concentrated. This gave 77 mg (21% of theory) of the title compound.

Workup

concentrationconcentrated
customThe residue was separated by means of preparative RP-HPLC (acetonitrile:water (+0.1% formic acid)−gradient)
concentrationthe product fractions were concentrated

Sources & evidence

ORD record: ord-d5597b296c2e485d9d9d3d0394760029
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309239B2

Reaction notes

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