Ethyl isocyanate → HCID 86598442, compound

HRID 1093011Notes

Reaction equation

HRID 1093011 reaction equation
Br.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([NH2:14])=[N:11][C:10]=2[CH3:15])=[CH:5][C:4]=1[S:16]([N:19]1[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]1)(=[O:18])=[O:17].CCN(C(C)C)C(C)C.[CH2:35]([N:37]=[C:38]=[O:39])[CH3:36]>CN(C=O)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([NH:14][C:38]([NH:37][CH2:35][CH3:36])=[O:39])=[N:11][C:10]=2[CH3:15])=[CH:5][C:4]=1[S:16]([N:19]1[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]1)(=[O:17])=[O:18]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 81531DiisopropylethylamineHCID 86598443HCID 86598443, compound

Product 1

HCID 86598442HCID 86598442, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A stirred solution of 5-[4-Chloro-3-(4-methyl-piperazine-1-sulfonyl)-phenyl]-4-methyl-thiazol-2-ylamine hydrobromide (174d) (0.1 g, 0.26 mmol) in DMF (1 ml) at room temperature is treated with DIPEA (0.07 g, 0.52 mmol) and ethyl isocyanate (0.025 ml, 0.33 mmol). The reaction mixture is heated to 120° C. for 1 hour and then allowed to cool to room temperature. Purification by preparative LC-MS affords the titled compound.

Workup

  1. temperatureto cool to room temperature
  2. customPurification by preparative LC-MS

Sources & evidence

ORD record
ord-5c3719c0643943b6ad697e945f30aff4
Source dataset
uspto-grants-2012_03
Patent number
US08129541B2

Reaction notes

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