HCID 10759063, compound → HCID 20622802, compound

HRID 2121234Notes

Reaction equation

HRID 2121234 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:6][C:5]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24].Cl.[CH3:27][O:28][C:29](=[O:36])[C@H:30]([CH2:32][CH2:33][S:34][CH3:35])[NH2:31]>>[CH3:27][O:28][C:29](=[O:36])[C@H:30]([CH2:32][CH2:33][S:34][CH3:35])[NH:31][C:3](=[O:2])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:6][C:5]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24]

Participants

3

Reactant 2

HCID 10759063HCID 10759063, compoundHCID 11435579L-Methionine, methyl ester, hydrochloride

Product 1

HCID 20622802HCID 20622802, compound

Procedure

The desired compound was prepared by saponification of 4-(3-pyridyloxymethyl)-2-(2-methylphenyl)benzoic acid methyl ester, prepared as in Example 204D, followed by coupling with methionine methyl ester hydrochloride and saponification as described in Examples 304E-G. 1H NMR (300 MHz, CDCl3) δ 8.40 (bs, 1H), 8.25 (dd, J=4.1, 1.9 Hz, 1H), 7.99 (dd, J=22.8, 8.1 Hz, 1H), 7.53-7.50 (m, 1H), 7.36-7.21 (m, 7H), 5.91 (bd, J=7.7 Hz, 1H (NH)), 5.18 (s, 2H), 4.70-4.58 (m, 1H), 3.66 (s, 3H, OMe), 2.18-2.00 (m, 5H), 1.95-1.82 (m, 1H), 1.65-1.55 (m, 4H, contains SMe). MS (CI) 465 (M+H)+. Anal calcd for C26H28O4N2S: 0.30H2O solvate: C, 66.45; H, 6.13; N, 5.96. Found: C, 66.45; H, 6.15; N, 5.97. HRMS FAB Calcd m/z MH+ for C26H28O4N2S 465.1848, found 465.1869.

Sources & evidence

ORD record
ord-2108c7dee94a4a3185c420ed780bf07b
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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