Diisopropylcarbodiimide → HCID 86674332, compound

HRID 1258653Notes

Reaction equation

HRID 1258653 reaction equation
[Cl:1][C:2]1[C:15]([N:16]=[C:17]=S)=[C:14]([Cl:19])[CH:13]=[CH:12][C:3]=1[CH2:4][NH:5][C:6](=[O:11])[C:7]([CH3:10])([CH3:9])[CH3:8].[Cl:20][C:21]1[C:27]([N:28]2[CH2:33][CH2:32][CH:31]([C:34]([F:37])([F:36])[F:35])[CH2:30][CH2:29]2)=[CH:26][C:24]([NH2:25])=[C:23]([NH:38]C)[CH:22]=1.[CH3:40]C(C)N=C=NC(C)C>CN(C=O)C>[Cl:1][C:2]1[C:15]([NH:16][C:17]2[N:25]([CH3:40])[C:24]3[CH:26]=[C:27]([N:28]4[CH2:33][CH2:32][CH:31]([C:34]([F:37])([F:36])[F:35])[CH2:30][CH2:29]4)[C:21]([Cl:20])=[CH:22][C:23]=3[N:38]=2)=[C:14]([Cl:19])[CH:13]=[CH:12][C:3]=1[CH2:4][NH:5][C:6](=[O:11])[C:7]([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 12734Diisopropylcarbodiimide2×HCID 56840192N-[(2,4-dichloro-3-isothiocyanatophenyl)methyl]-2,2-dimethylpropanamideHCID 67957790HCID 67957790, compound

Product 1

HCID 86674332HCID 86674332, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

N-(2,4-Dichloro-3-isothiocyanato-benzyl)-2,2-dimethyl-propionamide (120 mg, 0.4 mmol) was added to (4-chloro-2-methylamino-5-(4-trifluoromethyl-piperidin-1-yl)aniline (110 mg, 0.4 mmol) in DMF (2 mL). After 3 h at rt DIC (74 μL, 0.5 mmol) was added to the reaction mixture and it was stirred at 80° C. for 5.5 h. Additional DIC (40 μL, 0.3 mmol) was added and stirring was continued at 100° C. overnight. The reaction mixture was concentrated and the crude was purified by chromatography to give the title compound.

Workup

  1. stirringstirring
  2. waitwas continued at 100° C. overnight
  3. concentrationThe reaction mixture was concentrated
  4. customthe crude was purified by chromatography

Sources & evidence

ORD record
ord-bd59316510cb4a4f986006ba99b4b371
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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