Hydrochloric Acid → HCID 68903775, compound

HRID 1986303Notes

Reaction equation

HRID 1986303 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[C:15]3[CH:14]=[C:13]([C:16]4[C:21]([Cl:22])=[CH:20][N:19]=[C:18]([NH:23][CH2:24][CH2:25][CH2:26][N:27]5[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]5)[N:17]=4)[S:12][C:11]=3[C:10]([O:34]C)=[CH:9][CH:8]=2)=[O:6])[CH2:3][CH2:2]1.C(S)C.[H-].[Na+].Cl>CN(C=O)C.O>[CH:1]1([NH:4][C:5]([C:7]2[C:15]3[CH:14]=[C:13]([C:16]4[C:21]([Cl:22])=[CH:20][N:19]=[C:18]([NH:23][CH2:24][CH2:25][CH2:26][N:27]5[CH2:28][CH2:29][N:30]([CH3:33])[CH2:31][CH2:32]5)[N:17]=4)[S:12][C:11]=3[C:10]([OH:34])=[CH:9][CH:8]=2)=[O:6])[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 68857366HCID 68857366, compound

Product 1

HCID 68903775HCID 68903775, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-{5-chloro-2-[3-(4-methylpiperazin-1-yl)-propylamino]-pyrimidin-4-yl}-7-methoxybenzo[b]thiophene-4-carboxylic acid cyclopropylamide (500 mg, 0.970 mmol) and ethanethiol (0.718 mL, 9.71 mmol) in dry DMF (10 mL) is added in one portion sodium hydride (388 mg, 9.71 mmol) at 0° C. The mixture is stirred for 5 minutes and heated to 110° C. in a preheated oil bath for 10 minutes. The mixture is cooled to room temperature and a solution of HCl (12%, 3.5 mL) is added. The mixture is diluted with water (100 mL) and concentrated. The residue is diluted with MeOH and filtered off. The filtrate is purified on silica gel, eluting with dichloromethane in MeOH 90:10 to 60:40, to give the title compound as a yellow solid (116 mg, 24% yield). ES+(m/z) 501 (35Cl) and 503 (37Cl) [M+H].

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. concentrationconcentrated
  3. additionThe residue is diluted with MeOH
  4. filtrationfiltered off
  5. customThe filtrate is purified on silica gel
  6. washeluting with dichloromethane in MeOH 90:10 to 60:40

Sources & evidence

ORD record
ord-3bf05187856646e88359975d6f0df49b
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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