Ethyl isocyanate → HCID 178465353, compound

HRID 1819438Notes

Reaction equation

HRID 1819438 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][NH:9][C:10]2[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][N:13]=[C:12]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][C:28]([F:31])([F:30])[F:29])[N:11]=2)[CH2:4][CH2:3]1.[CH2:32]([N:34]=[C:35]=[O:36])[CH3:33]>CN(C=O)C>[CH2:32]([NH:34][C:35]([NH:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([CH2:8][NH:9][C:10]2[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][N:13]=[C:12]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][C:28]([F:30])([F:31])[F:29])[N:11]=2)[CH2:6][CH2:7]1)=[O:36])[CH3:33]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 178511544HCID 178511544, compound

Product 1

HCID 178465353HCID 178465353, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N4-[(trans-4-aminocyclohexyl)methyl]-5-nitro-N2-[2-(trifluoromethoxy)benzyl]-pyrimidine-2,4-diamine (100 mg, 0.23 mmol) in DMF (2 mL) was added ethyl isocyanate (65 mg, 0.91 mmol). The reaction mixture was stirred at room temperature for 16 h. The resulting precipitate was filtered and triturated in MeOH. The solid was dried in a vacuum oven to afford 47 mg (41%) of the title compound, m/z 512.7 [M +1]+

Workup

  1. filtrationThe resulting precipitate was filtered
  2. customtriturated in MeOH
  3. customThe solid was dried in a vacuum oven

Sources & evidence

ORD record
ord-d595f744caad46d49560ae92bb73bcb8
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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