Azetidine → 4-[5-(Azetidine-1-carbonyl)-pyrazin-2-yloxy]-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

HRID 1177374Notes

Reaction equation

HRID 1177374 reaction equation
CO[C:3]([C:5]1[CH:10]=[N:9][C:8]([O:11][C:12]2[C:17]3[CH2:18][C:19]([CH3:22])([CH3:21])[O:20][C:16]=3[CH:15]=[C:14]([C:23](=[O:31])[NH:24][C:25]3[CH:29]=[CH:28][N:27]([CH3:30])[N:26]=3)[CH:13]=2)=[CH:7][N:6]=1)=[O:4].[NH:32]1[CH2:35][CH2:34][CH2:33]1>CC(O)=O>[CH3:30][N:27]1[CH:28]=[CH:29][C:25]([NH:24][C:23]([C:14]2[CH:13]=[C:12]([O:11][C:8]3[CH:7]=[N:6][C:5]([C:3]([N:32]4[CH2:35][CH2:34][CH2:33]4)=[O:4])=[CH:10][N:9]=3)[C:17]3[CH2:18][C:19]([CH3:22])([CH3:21])[O:20][C:16]=3[CH:15]=2)=[O:31])=[N:26]1

Participants

4

Reactant 2

HCID 10422AzetidineHCID 59560421HCID 59560421, compound

Product 1

HCID 595602204-[5-(Azetidine-1-carbonyl)-pyrazin-2-yloxy]-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The title compound was prepared in a similar manner as described for Example 1, from 5-[2,2-dimethyl-6-(1-methyl-1H-pyrazol-3-ylcarbamoyl)-2,3-dihydro-benzofuran-4-yloxy]-pyrazine-2-carboxylic acid methyl ester (396a) and azetidine. 1H NMR (400 MHz, CDCl3) δ 8.86 (d, J=1.26 Hz, 1 H) 8.35 (d, J=1.26 Hz, 1 H) 8.30 (s, 1 H) 7.23-7.32 (m, 1 H) 7.18 (d, J=1.26 Hz, 1 H) 7.12 (d, J=1.26 Hz, 1 H) 6.79 (d, J=2.27 Hz, 1 H) 4.70 (t, J=7.83 Hz, 2 H) 4.27 (t, J=7.83 Hz, 2 H) 3.81 (s, 3 H) 2.85 (s, 2 H) 2.31-2.46 (m, 2 H) 1.49 (s, 6 H); LCMS for C23H24N6O4 m/z 449.20 (M+H+); Anal. Calcd. for C23H24N6O4.0.18 AcOH: C, 61.09; H, 5.43; N, 18.30. Found: C, 61.21; H, 5.64; N, 18.31.

Sources & evidence

ORD record
ord-05186c77fff445cc8c79e4dbdde2707c
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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