Lithium hydroxide, monohydrate → 4-[2-(2-Carbamimidoyl-5,6a,7,11b-tetrahydro-6H-indeno[2,1-c]quinolin-6-yl)-5-hydroxy-4-methoxy-phenoxy]-benzoic acid

HRID 2417391Notes

Reaction equation

HRID 2417391 reaction equation
C[O:2][C:3](=[O:40])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[C:15]([OH:17])[C:14]([O:18][CH3:19])=[CH:13][C:12]=2[CH:20]2[CH:29]3[CH2:30][C:31]4[C:36]([CH:28]3[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:37](=[NH:39])[NH2:38])[CH:26]=3)[NH:21]2)=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:6][CH:5]=1.O.[OH-].[Li+]>CO.O>[C:37]([C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]([C:12]1[CH:13]=[C:14]([O:18][CH3:19])[C:15]([OH:17])=[CH:16][C:11]=1[O:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:40])=[O:2])=[CH:9][CH:8]=1)[CH:29]1[CH2:30][C:31]3[C:36]([CH:28]21)=[CH:35][CH:34]=[CH:33][CH:32]=3)(=[NH:38])[NH2:39]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 698950294-[2-(2-Carbamimidoyl-5,6a,7,11b-tetrahydro-6H-indeno[2,1-c]quinolin-6-yl)-5-hydroxy-4-methoxy-phenoxy]-benzoic acid methyl ester

Product 1

HCID 226332754-[2-(2-Carbamimidoyl-5,6a,7,11b-tetrahydro-6H-indeno[2,1-c]quinolin-6-yl)-5-hydroxy-4-methoxy-phenoxy]-benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The mixture of 4-[2-(2-Carbamimidoyl-5,6a,7,11b-tetrahydro-6H-indeno[2,1-c]quinolin-6-yl)-5-hydroxy-4-methoxy-phenoxy]-benzoic acid methyl ester (54 mg, 0.1 mmol) and lithium hydroxide monohydrate (21 mg, 0.5 mmol) in 2.5 mL of MeOH and 1.5 mL of H2O was stirred at room temperature overnight. The desired product 4-[2-(2-Carbamimidoyl-5,6a,7,11b-tetrahydro-6H-indeno[2,1-c]quinolin-6-yl)-5-hydroxy-4-methoxy-phenoxy]-benzoic acid was purified using reverse phase HPLC. Mass spectrum 521 (M+1).

Workup

  1. customThe desired product 4-[2-(2-Carbamimidoyl-5,6a,7,11b-tetrahydro-6H-indeno[2,1-c]quinolin-6-yl)-5-hydroxy-4-methoxy-phenoxy]-benzoic acid was purified

Sources & evidence

ORD record
ord-b06fef9a8e9e4e54b6721d44ebea1c22
Source dataset
uspto-grants-2004_11
Patent number
US06825208B2

Reaction notes

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