Methyl chloroformate → HCID 87274557, compound

HRID 1869585Notes

Reaction equation

HRID 1869585 reaction equation
[CH:1]1([N:7]2[CH2:12][CH2:11][N:10]([C:13]3[S:17][C:16]([NH:18][C:19](=[O:28])[C:20]4[CH:25]=[CH:24][C:23](C=O)=[CH:22][CH:21]=4)=[N:15][C:14]=3[C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:36]([N:38](CC)CC)C.Cl[C:44]([O:46][CH3:47])=[O:45]>C1COCC1>[CH:1]1([N:7]2[CH2:8][CH2:9][N:10]([C:13]3[S:17][C:16]([NH:18][C:19](=[O:28])[C:20]4[CH:21]=[CH:22][C:23]([CH2:36][NH:38][C:44]([O:46][CH3:47])=[O:45])=[CH:24][CH:25]=4)=[N:15][C:14]=3[C:29]3[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=3)[CH2:11][CH2:12]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 57986740HCID 57986740, compound

Product 1

HCID 87274557HCID 87274557, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.15 g of the compound of Example 149 was dissolved in 10 ml of THF, 0.1 ml of triethylamine and a solution of 40 mg of methyl chloroformate in 2 ml of THF were sequentially added thereto under ice cooling, and the mixture was stirred at room temperature overnight. The reaction solution was concentrated, mixed with water, and extracted with EtOAc. The obtained organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure, and the thus-obtained residue was recrystallized from EtOAc to obtain 0.12 g of N-[5-(4-cyclohexylpiperazin-1-yl)-4-(4-fluorophenyl)thiazol-2-yl]-4-(methoxycarbonylaminomethyl)benzamide. The obtained compound was suspended in 5 ml of EtOAc, 0.6 ml of 0.4M HCl-EtOAc solution was added thereto under ice cooling, and the mixture was stirred overnight. The thus-precipitated solid was filtered and dried to obtain 115 mg of N-[5-(4-cyclohexylpiperazin-1-yl)-4-(4-fluorophenyl)thiazol-2-yl]-4-(methoxycarbonylaminomethyl)benzamide hydrochloride.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionmixed with water
  3. extractionextracted with EtOAc
  4. washThe obtained organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe solvent was concentrated under reduced pressure
  7. customthe thus-obtained residue was recrystallized from EtOAc

Sources & evidence

ORD record
ord-6a97780629cf4a7d830a3fc2ab8c28e0
Source dataset
uspto-grants-2009_12
Patent number
US07638536B2

Reaction notes

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