Methyl iodide → HCID 72550631, compound

HRID 512553Notes

Reaction equation

HRID 512553 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]3[S:13][C:14]([NH:20][C:21]([C:23]4[CH:27]=[CH:26][S:25][CH:24]=4)=[O:22])=[C:15]([C:17]([NH2:19])=[O:18])[N:16]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:28]([O-])([O-])=O.[K+].[K+].C[I:35]>CN(C=O)C>[I-:35].[C:17]([C:15]1[N:16]=[C:12]([NH:11][C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[N+:1]([CH3:28])=[CH:2][CH:3]=[CH:4]3)[S:13][C:14]=1[NH:20][C:21]([C:23]1[CH:27]=[CH:26][S:25][CH:24]=1)=[O:22])(=[O:18])[NH2:19]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86703386HCID 86703386, compound

Product 1

HCID 72550631HCID 72550631, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(quinolin-6-ylamino)-5-(thiophene-3-carboxamido)thiazole-4-carboxamide (50 mg, 0.126 mmol) in DMF (1 mL) was added K2CO3 (50 mg, 0.152 mmol) and. MeI (27 mg, 0.190 mmol) at rt. The mixture was stirred overnight at rt. The reaction was quenched by adding cold-water, and the reaction mixture was diluted with EtOAc. The resulting precipitates were collected by filtration and washed successively with EtOAc and water to afford 10 mg (15% yield) of the titled compound.

Workup

  1. customat rt
  2. customThe reaction was quenched
  3. additionby adding cold-water
  4. additionthe reaction mixture was diluted with EtOAc
  5. customThe resulting precipitates
  6. filtrationwere collected by filtration
  7. washwashed successively with EtOAc and water

Sources & evidence

ORD record
ord-2640a1966e9f4a77aa912810eec5a5e8
Source dataset
uspto-grants-2015_08
Patent number
US09102637B2

Reaction notes

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