3,4-Difluorobenzonitrile → HCID 67488938, compound

HRID 1643563Notes

Reaction equation

HRID 1643563 reaction equation
COC(C1C=C(OC2C=CC(S(C)(=O)=O)=CC=2)C=C2OC(C)CC=12)=O.[F:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1F)[C:30]#[N:31].[CH3:36][N:37]1[CH:41]=[CH:40][C:39]([NH:42][C:43]([C:45]2[CH:55]=[C:54]([OH:56])[C:48]3[CH2:49][C:50]([CH3:53])([CH3:52])[O:51][C:47]=3[CH:46]=2)=[O:44])=[N:38]1>>[CH3:36][N:37]1[CH:41]=[CH:40][C:39]([NH:42][C:43]([C:45]2[CH:55]=[C:54]([O:56][C:34]3[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][C:27]=3[F:26])[C:48]3[CH2:49][C:50]([CH3:53])([CH3:52])[O:51][C:47]=3[CH:46]=2)=[O:44])=[N:38]1

Participants

4

Reactant 3

HCID 5872033,4-DifluorobenzonitrileHCID 595600842,3-Dihydro-4-hydroxy-2,2-dimethyl-N-(1-methyl-1H-pyrazol-3-yl)-6-benzofurancarboxamideHCID 595604376-(4-Methanesulfonyl-phenoxy)-2-methyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester

Product 1

HCID 67488938HCID 67488938, compound

Procedure

The title compound was prepared in a similar manner as described for Intermediate 1f, from 3,4-difluorobenzonitrile (11 mg, 0.080 mmol) and 4-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid(1-methyl-1H-pyrazol-3-yl)-amide (31a) (23 mg, 0.080 mmol) to give a colorless oil (8 mg, 20% yield). 1H NMR (400 MHz, CDCl3) δ 8.49 (s, 1 H) 7.50 (dd, J=10.11, 1.77 Hz, 1 H) 7.42 (d, J=8.59 Hz, 1 H) 7.28 (d, J=2.02 Hz, 1 H) 7.00-7.08 (m, 2 H) 6.95 (s, 1 H) 6.77 (d, J=1.77 Hz, 1 H) 3.78 (s, 3 H) 2.97 (s, 2 H) 1.51 (s, 6 H); LCMS for C22H19FN4O3 m/z (M+H)+407.10.

Sources & evidence

ORD record
ord-b793b7daab1e413b94cdac4931f4dfed
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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