Methanol → HCID 59631079, compound

HRID 1431770Notes

Reaction equation

HRID 1431770 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:19][C:20]3[CH:21]=[C:22]([CH:27]=[C:28]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)[CH:29]=3)[C:23]([O:25]C)=[O:24])=[C:7]([CH3:18])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[N:9]2)=[CH:4][CH:3]=1.CO.[OH-].[Li+]>C1COCC1>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:19][C:20]3[CH:21]=[C:22]([CH:27]=[C:28]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)[CH:29]=3)[C:23]([OH:25])=[O:24])=[C:7]([CH3:18])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59631305HCID 59631305, compound

Product 1

HCID 59631079HCID 59631079, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared according to Procedure T using methyl 3-(7-fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-ylamino)-5-morpholinobenzoate (0.233 g, 0.493 mmol), methanol (2 mL), THF (3 mL), and 1 N aqueous lithium hydroxide (4.9 mL, 4.93 mmol). (Extraction was performed with 20% 2-propanol in chloroform rather than EtOAc). This afforded 3-((7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-amino)-5-(4-morpholinyl)benzoic acid as an orange amorphous solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.72-8.76 (1H, m), 8.13 (1H, m), 8.01-8.06 (1H, m), 7.89 (1H, dt, J=7.8, 1.2 Hz), 7.74-7.82 (1H, m), 7.49-7.56 (2H, m), 7.05 (1H, br. s.), 6.79 (1H, br. s.), 6.65 (1H, br. s.), 3.66-3.75 (4H, m), 3.06-3.11 (4H, m), 2.17 (3H, s). Mass Spectrum (ESI) m/e=459.0 (M+1).

Workup

  1. customPrepared
  2. extraction(Extraction

Sources & evidence

ORD record
ord-b2fb5ca1beb140faab26fd90cc5fb881
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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