1-Bromo-3-methanesulfonylpropane → (3-{5-Cyano-2-[(R)-6-methoxycarbonyl-7-methyl-3-oxo-8-(3-trifluoromethyl-phenyl)-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidin-5-yl]-phenyl}-propyl)-(3-methanesulfonyl-propyl)-dimethyl-ammonium formate

HRID 2203393Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[C@@H:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][C:12]=2[CH2:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])[N:9]2[C:25](=[O:28])[NH:26][N:27]=[C:8]2[N:7]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=2)[C:6]=1[CH3:39])=[O:4].Br[CH2:41][CH2:42][CH2:43][S:44]([CH3:47])(=[O:46])=[O:45]>CC#N>[CH:3]([O-:4])=[O:2].[C:17]([C:14]1[CH:15]=[CH:16][C:11]([C@H:10]2[N:9]3[C:25](=[O:28])[NH:26][N:27]=[C:8]3[N:7]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:37])([F:36])[F:38])[CH:30]=3)[C:6]([CH3:39])=[C:5]2[C:3]([O:2][CH3:1])=[O:4])=[C:12]([CH2:19][CH2:20][CH2:21][N+:22]([CH2:41][CH2:42][CH2:43][S:44]([CH3:47])(=[O:46])=[O:45])([CH3:24])[CH3:23])[CH:13]=1)#[N:18]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of Example 12 (150 mg, 0.28 mmol) in MeCN (2 mL) was added 1-bromo-3-methanesulfonyl-propane (225 mg, 1.12 mmol). The resulting mixture was heated at 90° C. for 40 minutes using microwave irradiation. The solvent was removed in vacuo and the resultant residue was purified by reverse phase chromatography (MDAP), giving the title compound as an off-white solid (65 mg)

Workup

custommicrowave irradiation
customThe solvent was removed in vacuo
customthe resultant residue was purified by reverse phase chromatography (MDAP)

Sources & evidence

ORD record: ord-e463bc89a36e4ad39ac774f7e77172df
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365577B2

Reaction notes

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