Methanol → HCID 59385203, compound

HRID 2356809Notes

Reaction equation

HRID 2356809 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][C:19]([C:22]([O:24]CCCC)=[O:23])=[C:18]([O:29][CH3:30])[CH:17]=4)=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1.FC1C=CC2N=C(NC3C=CC(C4C=CC(C(OC)=O)=C(OC)C=4)=CC=3)SC=2C=1.CO.[OH-].[Na+]>C1COCC1.O>[F:1][C:2]1[CH:32]=[CH:31][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[C:18]([O:29][CH3:30])[CH:17]=4)=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 59385329HCID 59385329, compoundHCID 59385335HCID 59385335, compound

Product 1

HCID 59385203HCID 59385203, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Butyl 4′-[(6-fluoro-1,3-benzothiazol-2-yl)amino]-3-methoxybiphenyl-4-carboxylate (0.30 g, 0.43 mmol) and methyl 4′-[(6-fluoro-1,3-benzothiazol-2-yl)amino]-3-methoxybiphenyl-4-carboxylate (0.13 g, 0.25 mmol) were combined in THF (6 mL), MeOH (6 mL) and water (3 mL), and then NaOH (0.09 g, 2.1 mmol) was added. The reaction mixture was heated at 50° C. for 3 h. Upon cooling to rt, the reaction mixture was concentrated under reduced pressure, acidified, and the resulting solid was collected by filtration. This yielded 0.286 g (87%) of the title compound. LC/MS m/z 395.2 (MH+), retention time 3.30 min. 1H NMR (400 MHz, DMSO-d6) δ 3.90 (s, 3H), 7.12-7.33 (m, 3H), 7.61-7.90 (m, 7H), 10.62 (br, 1H).

Workup

  1. temperatureUpon cooling to rt
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-7c107903f25442eeb52e1470a1906717
Source dataset
uspto-grants-2010_07
Patent number
US07759376B2

Reaction notes

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