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 1247497Notes

Reaction equation

HRID 1247497 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-930626e7cf2746fa9154ebb2e5536c50
Source dataset
uspto-grants-2006_10
Patent number
US07129249B2

Reaction notes

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