Water → HCID 66682452, compound

HRID 530312Notes

Reaction equation

HRID 530312 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[NH2:6][C:7]1[CH:8]=[C:9]([C:15]2[N:16]=[CH:17][N:18]([C:20]([N:22]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH3:23])=[O:21])[CH:19]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14].C(N(CC)CC)C.O>O1CCCC1>[CH:24]1([N:22]([CH3:23])[C:20]([N:18]2[CH:19]=[C:15]([C:9]3[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([NH:6][S:1]([CH3:4])(=[O:3])=[O:2])[CH:8]=3)[N:16]=[CH:17]2)=[O:21])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 666818744-(3-Amino-4-methoxyphenyl)-N-cyclohexyl-N-methyl-1H-imidazole-1-carboxamide

Product 1

HCID 66682452HCID 66682452, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Mesyl chloride (0.247 mL, 3.17 mmol) was added to a stirred solution of 4-(3-amino-4-methoxyphenyl)-N-cyclohexyl-N-methyl-1H-imidazole-1-carboxamide (1.04 g, 3.17 mmol) and triethylamine (0.441 mL, 3.17 mmol) in tetrahydrofuran (6 mL) at room temperature. The brown mixture was allowed to stir at room temperature over the weekend. Water was added and the solvent was evaporated. Then the aqueous layer was acidified and the residue was extracted with ethyl acetate. The aqueous layer was extracted twice with a mixture of dichloromethane/isopropanol (7:3). The organic layer was separated, dried (MgSO4) filtered and evaporated to give an off-white solid. The solid was recrystallised from an ethanol/dichloromethane mixture to give the product as an off-white solid (434 mg, 34%).

Workup

  1. customthe solvent was evaporated
  2. extractionthe residue was extracted with ethyl acetate
  3. extractionThe aqueous layer was extracted twice with a mixture of dichloromethane/isopropanol (7:3)
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto give an off-white solid
  9. customThe solid was recrystallised from an ethanol/dichloromethane mixture

Sources & evidence

ORD record
ord-2cb286f14c82435fa80e788cb36ff421
Source dataset
uspto-grants-2016_05
Patent number
US09353082B2

Reaction notes

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