Methyl iodide → HCID 178503678, compound

HRID 1403119Notes

Reaction equation

HRID 1403119 reaction equation
[F:1][CH:2]([F:47])[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([O:20][C@H:21]3[CH2:26][CH2:25][C@H:24]([NH:27][C:28](=[O:42])[C@@H:29]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:30][CH2:31][S:32][CH3:33])[CH2:23][CH2:22]3)[CH:9]=2)[C:6]2[CH:43]=[CH:44][CH:45]=[CH:46][C:5]=2[N:4]=1.[CH3:48][I:49]>>[I-:49].[C:37]([O:36][C:35]([NH:34][C@H:29]([C:28]([NH:27][C@H:24]1[CH2:23][CH2:22][C@H:21]([O:20][C:10]2[CH:9]=[C:8]([N:7]3[C:6]4[CH:43]=[CH:44][CH:45]=[CH:46][C:5]=4[N:4]=[C:3]3[CH:2]([F:1])[F:47])[N:13]=[C:12]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[N:11]=2)[CH2:26][CH2:25]1)=[O:42])[CH2:30][CH2:31][S+:32]([CH3:48])[CH3:33])=[O:41])([CH3:40])([CH3:38])[CH3:39]

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 178503714HCID 178503714, compound

Product 1

HCID 178503678HCID 178503678, compound

Procedure

To tert-butyl [(2S)-1-{[trans-4-({6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(morpholin-4-yl)pyrimidin-4-yl}oxy)cyclohexyl]amino}-4-(methylsulfanyl)-1-oxobutan-2-yl]carbamate (760 mg) was added methyl iodide (3.5 mL), followed by stirring at room temperature overnight. Methyl iodide was evaporated under reduced pressure to obtain a desired compound [(3S)-3-[(tert-butoxycarbonyl)amino]-4-{[trans-4-({6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(morpholin-4-yl)pyrimidin-4-yl}oxy)cyclohexyl]amino}-4-oxobutyl](dimethyl)sulfonium iodide (919 mg).

Workup

  1. customMethyl iodide was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d9846cecbe174a7b9e83f65ab9750273
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

Loading…