Trifluoroacetic acid → 4-(4-Methanesulfonyl-phenoxy)-2-methoxymethyl-2-methyl-2,3-dihydro-benzofuran-6-carboxylic acid (5-methyl-pyridin-2-yl)-amide

HRID 1177239Notes

Reaction equation

HRID 1177239 reaction equation
C([O:5][C:6]([C:8]1[CH:20]=[C:19]([O:21][C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=2)[C:11]2[CH2:12][C:13]([CH2:16][O:17][CH3:18])([CH3:15])[O:14][C:10]=2[CH:9]=1)=O)(C)(C)C.[CH3:32][C:33]1[CH:34]=[CH:35][C:36]([NH2:39])=[N:37][CH:38]=1.C(O)(C(F)(F)F)=O>>[CH3:32][C:33]1[CH:34]=[CH:35][C:36]([NH:39][C:6]([C:8]2[CH:20]=[C:19]([O:21][C:22]3[CH:23]=[CH:24][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:26][CH:27]=3)[C:11]3[CH2:12][C:13]([CH2:16][O:17][CH3:18])([CH3:15])[O:14][C:10]=3[CH:9]=2)=[O:5])=[N:37][CH:38]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 153482-Amino-5-methylpyridineHCID 595598574-(4-Methanesulfonyl-phenoxy)-2-methoxymethyl-2-methyl-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl ester

Product 1

HCID 595601534-(4-Methanesulfonyl-phenoxy)-2-methoxymethyl-2-methyl-2,3-dihydro-benzofuran-6-carboxylic acid (5-methyl-pyridin-2-yl)-amide

Procedure

The title compound was prepared in a similar manner as described for Example 200, from 4-(4-methanesulfonyl-phenoxy)-2-methoxymethyl-2-methyl-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl ester (228a) and 5-methyl-pyridin-2-ylamine. 1H NMR (400 MHz, CDCl3) δ 8.21 (d, J=8.59 Hz, 1 H) 8.09 (s, 1 H) 7.92 (ddd, J=9.22, 2.78, 2.40 Hz, 2 H) 7.65 (dd, J=8.59, 2.02 Hz, 1 H) 7.19 (s, 1 H) 7.13 (s, 2 H) 7.09-7.11 (m, 1 H) 3.43-3.53 (m, 2 H) 3.41 (s, 3 H) 3.16 (d, J=16.42 Hz, 1 H) 3.06-3.10 (m, 3 H) 2.80 (d, J=16.67 Hz, 1 H) 2.34 (s, 3 H) 1.48 (s, 3 H); LCMS for C25H26N2O6S m/z 483.00 (M+H)+; Anal. Calcd. for C25H26N2O6S.0.37 TFA: C, 58.95; H, 5.18; N, 5.34. Found: C, 58.92; H, 5.07; N, 5.34.

Sources & evidence

ORD record
ord-565201c6062f49e88043fcd21592edc2
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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