4-hydroxy-2-methoxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide → 4-(4-Dimethylcarbamoyl-3-fluoro-phenoxy)-2-methoxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

HRID 1643677Notes

Reaction equation

HRID 1643677 reaction equation
COC(C1C=C(OC2C=CC(S(C)(=O)=O)=CC=2)C=C2OC(C)CC=12)=O.[CH3:26][N:27]1[CH:31]=[CH:30][C:29]([NH:32][C:33]([C:35]2[CH:46]=[C:45]([OH:47])[C:38]3[CH2:39][CH:40]([CH2:42][O:43][CH3:44])[O:41][C:37]=3[CH:36]=2)=[O:34])=[N:28]1.[F:48][C:49]1[CH:59]=[C:58](F)[CH:57]=[CH:56][C:50]=1[C:51]([N:53]([CH3:55])[CH3:54])=[O:52]>O>[CH3:26][N:27]1[CH:31]=[CH:30][C:29]([NH:32][C:33]([C:35]2[CH:46]=[C:45]([O:47][C:58]3[CH:57]=[CH:56][C:50]([C:51](=[O:52])[N:53]([CH3:55])[CH3:54])=[C:49]([F:48])[CH:59]=3)[C:38]3[CH2:39][CH:40]([CH2:42][O:43][CH3:44])[O:41][C:37]=3[CH:36]=2)=[O:34])=[N:28]1

Participants

5

Reactant 3

HCID 595601864-hydroxy-2-methoxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amideHCID 595604376-(4-Methanesulfonyl-phenoxy)-2-methyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl esterHCID 606372302,4-difluoro-N,N-dimethylbenzamide

Product 1

HCID 595603094-(4-Dimethylcarbamoyl-3-fluoro-phenoxy)-2-methoxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared in a similar manner as described for Intermediate 1f, from 4-hydroxy-2-methoxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide (204d) and 2,4-difluoro-N,N-dimethyl-benzamide. 1H NMR (400 MHz, DMSO-d6) δ 10.75 (s, 1 H) 7.58 (d, J=1.77 Hz, 1 H) 7.40 (t, J=8.21 Hz, 1 H) 7.26 (s, 1 H) 7.21 (s, 1 H) 7.00 (dd, J=11.12, 1.52 Hz, 1 H) 6.91 (dd, J=8.46, 1.89 Hz, 1 H) 6.54 (d, J=1.52 Hz, 1 H) 5.01-5.09 (m, 1 H) 3.76 (s, 3 H) 3.50-3.59 (m, 2 H) 3.29 (s, 3 H) 3.10-3.21 (m, 1 H) 2.99 (s, 3 H) 2.85-2.89 (m, 4 H); LCMS for C24H25FN4O5 m/z 469.20 (M+H)+; Anal. Calcd. for C24H25FN4O5.0.63 H2O: C, 60.08; H, 5.52; N, 11.68; Found: C, 60.08; H, 5.19; N, 11.53.

Sources & evidence

ORD record
ord-f377b0fea6e641b0852acafd16e7bb6c
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

Loading…