Water → HCID 46832297, compound

HRID 530313Notes

Reaction equation

HRID 530313 reaction equation
C1(C)C=CC=CC=1.[C:8](Cl)(Cl)=[O:9].[NH2:12][C:13]1[CH:14]=[C:15]([C:20]2[N:21]=[CH:22][N:23]([C:25]([N:27]([CH:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)[CH3:28])=[O:26])[CH:24]=2)[CH:16]=[CH:17][C:18]=1[OH:19].O>ClCCl.ClCCl.C(O)(C)C>[CH:29]1([N:27]([CH3:28])[C:25]([N:23]2[CH:24]=[C:20]([C:15]3[CH:16]=[CH:17][C:18]4[O:19][C:8](=[O:9])[NH:12][C:13]=4[CH:14]=3)[N:21]=[CH:22]2)=[O:26])[CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

7

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 6371PhosgeneHCID 66682150HCID 66682150, compound

Product 1

HCID 46832297HCID 46832297, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21966342Isopropanol methylene chlorideSolvent

Procedure

A 20% toluene solution of phosgene (0.590 mL, 1.121 mmol) was added dropwise at room temperature to a stirred solution of 4-(3-amino-4-hydroxyphenyl)-N-cyclopentyl-N-methyl-1H-imidazole-1-carboxamide (0.259 g, 0.862 mmol) in dichloromethane (5 mL) and the off-white suspension was allowed to stir for 5 h. Water was added and the organic layer was diluted with a mixture of dichloromethane/isopropanol (7:3). The organic layer was separated, dried (MgSO4), filtered and evaporated to give an off-white solid that was triturated with hot methanol. Filtration and drying gave the product as an off-white solid (90 mg, 30%).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto give an off-white solid
  6. customthat was triturated with hot methanol
  7. filtrationFiltration
  8. customdrying

Sources & evidence

ORD record
ord-33106bc241cd4cc599df66f47b315f6c
Source dataset
uspto-grants-2016_05
Patent number
US09353082B2

Reaction notes

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