Lithium Hydroxide → N-[1-(Carboxymethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide

HRID 1178414Notes

Reaction equation

HRID 1178414 reaction equation
[Li+].[OH-].[Cl:3][C:4]1[S:30][C:7]2[NH:8][C:9]([C:11]([NH:13][CH:14]3[CH2:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]([CH2:24][C:25]([O:27]C)=[O:26])[C:15]3=[O:29])=[O:12])=[CH:10][C:6]=2[CH:5]=1>O.C1COCC1>[C:25]([CH2:24][N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:23][CH:14]([NH:13][C:11]([C:9]2[NH:8][C:7]3[S:30][C:4]([Cl:3])=[CH:5][C:6]=3[CH:10]=2)=[O:12])[C:15]1=[O:29])([OH:27])=[O:26]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 100020612-Chloro-N-[1-(methoxycarbonylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide

Product 1

HCID 10319016N-[1-(Carboxymethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamideYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH (1.41 g, 33.6 mmol) in H2O (16.5 mL) was added to a stirring solution of 2-chloro-N-[1-(methoxycarbonylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide (Example 1; 7.00 g, 16.8 mmol) in THF (88 mL) and the reaction was stirred for 2 h. The reaction was quenched by addition of 1M aqueous HCl (200 mL) and EtOAc (400 mL) and the organic layer was dried (MgSO4), filtered and evaporated. The resultant white foam was triturated with hot Et2O (100 mL) cooled, filtered and dried to afford the title compound (6.00 g, 89%) as a white solid.

Workup

  1. customThe reaction was quenched by addition of 1M aqueous HCl (200 mL) and EtOAc (400 mL)
  2. dry with materialthe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe resultant white foam was triturated with hot Et2O (100 mL)
  6. temperaturecooled
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-8b2141ab63314e2b8fa03edbc8f32c28
Source dataset
uspto-grants-2007_10
Patent number
US07276517B2

Reaction notes

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