Hydrochloric Acid → HCID 68535253, compound

HRID 644279Notes

Reaction equation

HRID 644279 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:36])[C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18]C)=[O:17])=[CH:12][C:11]=2[NH:20][C:21](=[O:35])[C:22]2[CH:27]=[CH:26][C:25]([S:28][CH3:29])=[CH:24][C:23]=2[O:30][CH2:31][CH2:32][CH2:33][NH2:34])=[N:6][CH:7]=1.CO.[Li+].[OH-].Cl>O>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:36])[C:10]2[CH:15]=[CH:14][C:13]([C:16]([OH:18])=[O:17])=[CH:12][C:11]=2[NH:20][C:21](=[O:35])[C:22]2[CH:27]=[CH:26][C:25]([S:28][CH3:29])=[CH:24][C:23]=2[O:30][CH2:31][CH2:32][CH2:33][NH2:34])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 57860777HCID 57860777, compound

Product 1

HCID 68535253HCID 68535253, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To a mixture of N-(5-chloropyridin-2-yl)-4-methoxycarbonyl-2-[4-methylthio-2-(3-aminopropoxy)benzoylamino]benzamide (480 mg, 0.91 mmol), MeOH (10 mL) and water (7 mL) was added LiOH (109 mg, 4.54 mmol). The reaction mixture was heated to 65° C. for 45 min and then cooled to room temperature. To the mixture was added 5N HCl (1.8 mL, 9 mmol), and the resulting solid was filtered with CH2Cl2 and 20% Et2O/hexanes washes to give the title compound as a white solid (213 mg, 55%).

Workup

  1. temperaturecooled to room temperature
  2. filtrationthe resulting solid was filtered with CH2Cl2 and 20% Et2O/hexanes washes

Sources & evidence

ORD record
ord-69ab6c9ea71f4fc9abae771cc021721a
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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