Methyl chloroformate → Nelociguat

HRID 346537Notes

Reaction equation

Cl.Cl.Cl.[F:4][C:5]1[CH:29]=[CH:28][CH:27]=[CH:26][C:6]=1[CH2:7][N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C:10]([C:17]2[N:22]=[C:21]([NH2:23])[C:20]([NH2:24])=[C:19]([NH2:25])[N:18]=2)=[N:9]1.Cl[C:31]([O:33][CH3:34])=[O:32]>N1C=CC=CC=1>[NH2:25][C:19]1[C:20]([NH:24][C:31](=[O:32])[O:33][CH3:34])=[C:21]([NH2:23])[N:22]=[C:17]([C:10]2[C:11]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[N:8]([CH2:7][C:6]3[CH:26]=[CH:27][CH:28]=[CH:29][C:5]=3[F:4])[N:9]=2)[N:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

30.5 g (87.0 mmol) of 2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4,5,6-pyrimidinetriamine trihydrochloride from Example 8A are dissolved in 30 ml of pyridine. The resulting solution is cooled to 0° C. 8.22 g (87.0 mmol) of methyl chloroformate are added, and the mixture is stirred at 0° C. for a further 2 hours. It is subsequently allowed to warm to room temperature and is stirred for a further 12 hours. After concentration in vacuo, the residue is washed with water and dried. Further purification is effected by stirring in 300 ml of boiling diethyl ether. The precipitated product is filtered off with suction and dried in vacuo.

Workup

temperatureto warm to room temperature
stirringis stirred for a further 12 hours
concentrationAfter concentration in vacuo
washthe residue is washed with water
customdried
customFurther purification
stirringby stirring in 300 ml of boiling diethyl ether
filtrationThe precipitated product is filtered off with suction
customdried in vacuo

Sources & evidence

ORD record: ord-eb9039af0a234a438b689d17ff8871c4
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07173037B2

Reaction notes

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