Sodium Hydroxide → HCID 71239397, compound

HRID 1424302Notes

Reaction equation

HRID 1424302 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][CH2:5][NH:6][C:7](=[O:34])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH:28]2[CH2:31][C:30]([CH3:33])([CH3:32])[CH2:29]2)[NH:15][C:16]2[C:25]([CH3:26])=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([F:27])[CH:22]=3)[N:17]=2)=[CH:10][CH:9]=1.[OH-].[Na+]>CO.C1COCC1>[CH3:32][C:30]1([CH3:33])[CH2:31][CH:28]([CH:14]([NH:15][C:16]2[C:25]([CH3:26])=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([F:27])[CH:22]=3)[N:17]=2)[C:11]2[CH:10]=[CH:9][C:8]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:35])=[O:2])=[O:34])=[CH:13][CH:12]=2)[CH2:29]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71239336HCID 71239336, compound

Product 1

HCID 71239397HCID 71239397, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The title compound was prepared by treating 3-{4-[(3,3-Dimethyl-cyclobutyl)-(6-fluoro-3-methyl-quinolin-2-ylamino)-methyl]-benzoylamino}-propionic acid methyl ester, isomer 1, (intermediate 74) with 1N NaOH (2.5 eq.) in methanol/THF in a similar manner as described in Example 19 to provide the title compound. Analytical chiral SFC: (Chiralpak IC column, 4.6 mm×25 cm, 25% methanol/carbon dioxide eluent, 2.5 mL/min flow rate, 4.33 retention time); 1H NMR (400 MHz, DMSO-d6) δ 12.14 (s, 1H), 8.38 (br. s., 1H), 7.63-7.76 (m, 3H), 7.55 (d, J=7.8 Hz, 2H), 7.39-7.50 (m, 1H), 7.30-7.39 (m, 1H), 7.21-7.30 (m, 1H), 6.45-6.60 (m, 1H), 5.11-5.28 (m, 1H), 3.41 (dd, J=12.7, 7.1 Hz, 2H), 2.75-2.91 (m, 1H), 2.46 (t, J=7.1 Hz, 2H), 2.29 (s, 3H), 1.92-2.00 (m, 1H), 1.56-1.67 (m, 2H), 1.42-1.55 (m, 1H), 1.12 (s, 3H), 1.07 (s, 3H); MS (M+1): 464.3.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-fb361b906ce24a9cb50e16f174a2f140
Source dataset
uspto-grants-2015_01
Patent number
US08927577B2

Reaction notes

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