Dimethylamine, hydrochloride → 5-[2,2-Dimethyl-6-(1-methyl-1H-pyrazol-3-ylcarbamoyl)-2,3-dihydro-benzofuran-4-yloxy]-3-fluoro-pyridine-2-carboxylic acid dimethylamide

HRID 1177157Notes

Reaction equation

Cl.[CH3:2][NH:3][CH3:4].CO[C:7]([C:9]1[C:14]([F:15])=[CH:13][C:12]([O:16][C:17]2[C:22]3[CH2:23][C:24]([CH3:27])([CH3:26])[O:25][C:21]=3[CH:20]=[C:19]([C:28](=[O:36])[NH:29][C:30]3[CH:34]=[CH:33][N:32]([CH3:35])[N:31]=3)[CH:18]=2)=[CH:11][N:10]=1)=[O:8]>>[CH3:2][N:3]([CH3:4])[C:7]([C:9]1[C:14]([F:15])=[CH:13][C:12]([O:16][C:17]2[C:22]3[CH2:23][C:24]([CH3:27])([CH3:26])[O:25][C:21]=3[CH:20]=[C:19]([C:28](=[O:36])[NH:29][C:30]3[CH:34]=[CH:33][N:32]([CH3:35])[N:31]=3)[CH:18]=2)=[CH:11][N:10]=1)=[O:8]

Participants

Reactant 2

HCID 10473Dimethylamine, hydrochloride

HCID 59559964Methyl 5-[[2,3-dihydro-2,2-dimethyl-6-[[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl]-4-benzofuranyl]oxy]-3-fluoro-2-pyridinecarboxylate

Product 1

HCID 595604305-[2,2-Dimethyl-6-(1-methyl-1H-pyrazol-3-ylcarbamoyl)-2,3-dihydro-benzofuran-4-yloxy]-3-fluoro-pyridine-2-carboxylic acid dimethylamide

Procedure

The title compound was prepared in a similar manner as described for Example 1, from dimethyl amine hydrochloride (278 mg, 3.41 mmol) and 5-[2,2-dimethyl-6-(1-methyl-1H-pyrazol-3-ylcarbamoyl)-2,3-dihydro-benzofuran-4-yloxy]-3-fluoro-pyridine-2-carboxylic acid methyl ester (175b) (150 mg, 0.341 mmol) to give a white solid (74 mg, 48% yield). 1H NMR (400 MHz, CDCl3) δ 8.39 (s, 1 H) 8.22 (d, J=1.77 Hz, 1 H) 7.27-7.31 (m, 1 H) 7.01-7.13 (m, 3 H) 6.78 (d, J=2.02 Hz, 1 H) 3.81 (s, 3 H) 3.16 (s, 3 H) 3.00 (s, 3 H) 2.92 (s, 2 H) 1.50 (s, 6 H); LCMS for C23H24FN5O4 m/z 454.20 (M+H+); Anal. Calcd. for C23H24FN5O4: C, 60.92; H, 5.33; N, 15.44. Found: C, 60.66; H, 5.37; N, 15.26.

Sources & evidence

ORD record: ord-87abb7873a8a4077ab213b2a357e5452
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842713B2

Reaction notes

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