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

HRID 1528679Notes

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][CH:32]([CH3:34])[CH3:33])=[O:30]>N1C=CC=CC=1>[NH2:19][C:13]1[C:14]([NH:18][C:29](=[O:30])[O:31][CH:32]([CH3:34])[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

300 mg (0.81 mmol) of the compound from example 8A were initially charged in 10 ml of pyridine, and the mixture was cooled to 0° C. 0.81 ml (0.81 mmol) of isopropyl chloroformate was then added dropwise, and the mixture was stirred at 0° C. for a further 60 min. The reaction mixture was brought to RT and purified directly by means of preparative RP-HPLC (acetonitrile:water (+0.1% formic acid) gradient). This gave 88 mg of the target compound (24% of theory).

Workup

customwas brought to RT
custompurified directly by means of preparative RP-HPLC (acetonitrile:water (+0.1% formic acid) gradient)

Sources & evidence

ORD record: ord-37ab9e0e43a9486db54ca78ed54299b4
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090609B2

Reaction notes

Loading…