Methylamine → HCID 72550630, compound

HRID 512552Notes

Reaction equation

HRID 512552 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH:11][C:12]1[S:13][C:14]([NH:22][C:23]([C:25]2[CH:29]=[CH:28][S:27][CH:26]=2)=[O:24])=[C:15]([C:17]([O:19]CC)=O)[N:16]=1.[CH3:30][NH2:31]>C1COCC1.O>[CH3:30][NH:31][C:17]([C:15]1[N:16]=[C:12]([NH:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[S:13][C:14]=1[NH:22][C:23]([C:25]1[CH:29]=[CH:28][S:27][CH:26]=1)=[O:24])=[O:19]

Participants

5

Reactant 2

HCID 6329Methylamine2×HCID 86703385Ethyl 2-(naphthalen-2-ylamino)-5-(thiophene-3-carboxamido)thiazole-4-carboxylate

Product 1

HCID 72550630HCID 72550630, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(naphthalen-2-ylamino)-5-(thiophene-3-carboxamido)thiazole-4-carboxylate (50 mg, 0.118 mmol) in THF (5 mL) was added 40% methylamine in water (0.5 mL) at rt, and the mixture was stirred overnight at rt. To complete the reaction, an additional 40% methylamine in water (0.5 mL) was added to the mixture, and stirring was continued at rt overnight. The solvent was removed, and the residue was triturated with water. The resulting solids were collected by filtration, and the solids were washed successively with water and EtOAc to give 28 mg (58% yield) of the titled compound.

Workup

  1. customthe reaction
  2. stirringstirring
  3. waitwas continued at rt overnight
  4. customThe solvent was removed
  5. customthe residue was triturated with water
  6. filtrationThe resulting solids were collected by filtration
  7. washthe solids were washed successively with water and EtOAc

Sources & evidence

ORD record
ord-88aedbd4e3984360b5109c3140ed0ded
Source dataset
uspto-grants-2015_08
Patent number
US09102637B2

Reaction notes

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