Hydrochloric Acid → HCID 71061723, compound

HRID 875449Notes

Reaction equation

HRID 875449 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:29])[C:11]=1[C:12]([C:14]1[C:22]2[C:17](=[C:18]([NH:23][C:24]([CH:26]3[CH2:28][CH2:27]3)=[O:25])[N:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)=[O:13])[C:5]([O:7]C)=[O:6].[OH-].[Na+].O.Cl>O1CCCC1>[Cl:29][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([Cl:1])[C:11]=1[C:12]([C:14]1[C:22]2[C:17](=[C:18]([NH:23][C:24]([CH:26]3[CH2:28][CH2:27]3)=[O:25])[N:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)=[O:13])[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86720651HCID 86720651, compound

Product 1

HCID 71061723HCID 71061723, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 3,5-dichloro-4-({7-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)benzoate, (30 mg, 0.06 mmol) and sodium hydroxide (27 mg, 0.06 mmol) were stirred in tetrahydrofuran and water (1:1, 6 mL) solution for about 2 hours, followed by slowly addition of aqueous hydrochloric acid till pH 4-5. The precipitated product was filtered and dried under vacuum to afford 3,5-dichloro-4-({7-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)benzoic acid (20 mg, 62.5%).

Workup

  1. filtrationThe precipitated product was filtered
  2. customdried under vacuum

Sources & evidence

ORD record
ord-7fb658064fb74e59ade23932d9cab42f
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

Loading…