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

HRID 1888892Notes

Reaction equation

S(C)(C)=O.[NH2:5][C:6]1[C:11]([NH:12][C:13](=[O:16])[O:14][CH3:15])=[C:10]([NH2:17])[N:9]=[C:8]([C:18]2[C:26]3[C:21](=[N:22][CH:23]=[CH:24][CH:25]=3)[N:20]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[F:34])[N:19]=2)[N:7]=1>C(OCC)(=O)C.C(O)C>[NH2:5][C:6]1[C:11]([NH:12][C:13](=[O:16])[O:14][CH3:15])=[C:10]([NH2:17])[N:9]=[C:8]([C:18]2[C:26]3[C:21](=[N:22][CH:23]=[CH:24][CH:25]=3)[N:20]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[F:34])[N:19]=2)[N:7]=1

Participants

Conditions

Temperature: 73.5 °C

Procedure

7.1 kg of the product of the formula (II) were suspended in 171.6 kg of ethyl acetate and 42 kg of ethanol, and the mixture was stirred at reflux (internal temperature about 73-74° C.) for 20 h. The suspension was cooled to RT and filtered off with suction, and the product was washed four times with in each case 12.2 kg of ethyl acetate. The product was then washed twice with in each case 12.2 kg of water to expel the ethyl acetate, and the moist product was dried under reduced pressure at 50° C. until its mass remained constant. The yield of pure product of the formula (I) was 4.3 kg or 84% of theory. The content of the product was more than 99% (HPLC).

Workup

temperatureThe suspension was cooled to RT
filtrationfiltered off with suction
washthe product was washed four times with in each case 12.2 kg of ethyl acetate
washThe product was then washed twice with in each case 12.2 kg of water
customthe moist product was dried under reduced pressure at 50° C. until its mass

Sources & evidence

ORD record: ord-7245a07bea84449bbc0ed6225261b87d
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501945B2

Reaction notes

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