Methanesulfonyl chloride → 3-(4-(5-Amino-6-(pyridin-3-ylcarbamoyl)pyrazin-2-yl)phenyl)propyl methanesulfonate

HRID 217774Notes

Reaction equation

C(N(C(C)C)CC)(C)C.[NH2:10][C:11]1[C:12]([C:27]([NH:29][C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)=[O:28])=[N:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][OH:26])=[CH:19][CH:18]=2)=[CH:15][N:16]=1.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>ClCCl>[CH3:36][S:37]([O:26][CH2:25][CH2:24][CH2:23][C:20]1[CH:21]=[CH:22][C:17]([C:14]2[CH:15]=[N:16][C:11]([NH2:10])=[C:12]([C:27](=[O:28])[NH:29][C:30]3[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=3)[N:13]=2)=[CH:18][CH:19]=1)(=[O:39])=[O:38]

Participants

Conditions

Temperature: 0 °C

Procedure

Dichloromethane (200 mL) and diisopropylethylamine (2 g, 17.16 mmol) were added to the product of step (vii) (4 g, 11.46 mmol). The resulting solution was cooled to 0° C. and MsCl (2 g, 17.16 mmol) added dropwise. When the addition was completed, the resulting solution was stirred at 0° C. for 10 minutes and at room temperature for 2 hours. The reaction mixture was extracted with dichloromethane and washed with water (×3). The combined organic extract was dried over MgSO4, filtered and concentrated in vacuo, which afforded the subtitle compound (viii) as a yellow brown solid (4.5 g).

Workup

additionWhen the addition
extractionThe reaction mixture was extracted with dichloromethane
washwashed with water (×3)
extractionThe combined organic extract
dry with materialwas dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo, which

Sources & evidence

ORD record: ord-8d97df8e561847cb958b24069779303f
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198285B2

Reaction notes

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