2-Aminothiazole → HCID 11472408, compound

HRID 1685554Notes

Reaction equation

HRID 1685554 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=O)=[CH:2]1.CCN=C=NCCCN(C)C.C1[CH:25]=[CH:26][C:27]2N(O)N=N[C:28]=2[CH:29]=1.[NH2:34][C:35]1[S:36][CH:37]=[CH:38][N:39]=1>CN1C(=O)CCC1>[S:36]1[CH:37]=[CH:38][N:39]=[C:35]1[NH:34][C:10]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:1]([CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)[CH:2]=1)=[O:12]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69867Indole-3-Carboxylic AcidHCID 757711-Hydroxybenzotriazole

Product 1

HCID 11472408HCID 11472408, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

The crude derivative of indole-3-carboxylic acid was dissolved in NMP (5 mL). EDAC (1.09 g, 5.7 mmol) and HOBt (0.92 g, 6.84 mmol) were added. The mixture was stirred at room temperature for 1 hour before 2-aminothiazole (5.7 mmol) was added. The mixture was heated to 120° C. for 2 hours. After cooling to room temperature the reaction mixture was separated between diethyl ether (50 mL) and water (50 mL). The organic phase was washed with saturated aqueous Na2CO3 (50 mL), dried (Na2SO4) and the solvent removed in vacuo. The crude material was recrystallized from acetonitrile to give the title compound.

Workup

  1. additionwas added
  2. temperatureAfter cooling to room temperature the reaction mixture
  3. customwas separated between diethyl ether (50 mL) and water (50 mL)
  4. washThe organic phase was washed with saturated aqueous Na2CO3 (50 mL)
  5. dry with materialdried (Na2SO4)
  6. customthe solvent removed in vacuo
  7. customThe crude material was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-64da6a08d0a6414c8aafe14b8d70040d
Source dataset
uspto-grants-2012_04
Patent number
US08148413B2

Reaction notes

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