Methylamine → HCID 72550635, compound

HRID 512558Notes

Reaction equation

HRID 512558 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:20][C:21](=[O:36])[CH2:22][CH2:23][CH2:24][N:25]2C(=O)C3=CC=CC=C3C2=O)=[C:15]([C:17]([NH2:19])=[O:18])[N:16]=1.CN>CCO>[NH2:25][CH2:24][CH2:23][CH2:22][C:21]([NH:20][C:14]1[S:13][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)=[N:16][C:15]=1[C:17]([NH2:19])=[O:18])=[O:36]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86703389HCID 86703389, compound

Product 1

HCID 72550635HCID 72550635, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-(naphthalen-2-ylamino)-5-(4-phthalimidobutanamido)thiazole-4-carboxamide (180 mg, 0.36 mmol) and 33% methylamine in EtOH (5 mL) was heated at 70° C. for 4 hrs. The solvent was removed, and water was added to the residual oil. The resulting solids were collected by filtration and washed successively with ether, DCM and MeOH to give 38 mg (29% yield) of the titled compound.

Workup

  1. customThe solvent was removed
  2. additionwater was added to the residual oil
  3. filtrationThe resulting solids were collected by filtration
  4. washwashed successively with ether, DCM and MeOH

Sources & evidence

ORD record
ord-7983765c37e345ce8a92c7a471b01da7
Source dataset
uspto-grants-2015_08
Patent number
US09102637B2

Reaction notes

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