Ammonia → HCID 54495970, compound

HRID 2121247Notes

Reaction equation

HRID 2121247 reaction equation
CO[C:3](=[O:26])[C:4]1[CH:9]=[C:8]([I:10])[C:7]([CH2:11][O:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:6][C:5]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:25].Cl.C[O:29][C:30](=[O:37])[C@H:31]([CH2:33][CH2:34][S:35][CH3:36])[NH2:32].N>>[N:15]1[CH:16]=[CH:17][CH:18]=[C:13]([O:12][CH2:11][C:7]2[C:8]([I:10])=[CH:9][C:4]([C:3]([NH:32][C@H:31]([C:30]([OH:37])=[O:29])[CH2:33][CH2:34][S:35][CH3:36])=[O:26])=[C:5]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH3:25])[CH:6]=2)[CH:14]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 10575895HCID 10575895, compoundHCID 11435579L-Methionine, methyl ester, hydrochloride

Product 1

HCID 54495970HCID 54495970, compound

Procedure

The desired compound was prepared by saponification of 4-(3-pyridyloxymethyl)-5-iodo-2-(2-methylphenyl)benzoic acid methyl ester, prepared as in Example 219G, followed by coupling with methionine methyl ester hydrochloride and saponification of the methyl ester as described above. 1H NMR (300 MHz, DMSO-d6) δ 12.68 (1H, bs), 8.45 (1H, d, J=9 Hz), 8.37 (1H, d, J=3 Hz), 8.20 (1H, d, J=4 Hz), 7.93 (1H, s), 7.48 (1H, m), 7.37 (2H, m), 7.30-7.00 (4H, m), 5.20 (2H, s), 4.22 (1H, m), 2.30-2.00 (5H, m), 1.96 (3H, s), 1.80 (2H, m). MS m/e (DCI, NH3) m/e 577 (M+H)+. Anal calcd for C25H25IN2O4S: C, 51.85; H, 4.40; N, 4.84. Found: C, 51.91; H, 4.47; N, 4.69.

Sources & evidence

ORD record
ord-1c4e920e6fd548f0b182496f3239a26a
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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