2-(4,4-Difluorocyclohexyl)acetic acid → Tert-butyl[(3-{[(4,4-difluorocyclohexyl)acetyl]amino}-4-oxo-3,4-dihydrophthalazin-1-yl)methyl]carbamate

HRID 535547Notes

Reaction equation

HRID 535547 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[N:11]([NH2:20])[N:10]=1)([CH3:4])([CH3:3])[CH3:2].[F:22][C:23]1([F:33])[CH2:28][CH2:27][CH:26]([CH2:29][C:30](O)=[O:31])[CH2:25][CH2:24]1>>[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[N:11]([NH:20][C:30](=[O:31])[CH2:29][CH:26]2[CH2:27][CH2:28][C:23]([F:33])([F:22])[CH2:24][CH2:25]2)[N:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 534207432-(4,4-Difluorocyclohexyl)acetic acidHCID 131731940Tert-butyl(3-amino-4-oxo-3,4-dihydrophthalazin-1-yl)methylcarbamate

Product 1

HCID 123307834Tert-butyl[(3-{[(4,4-difluorocyclohexyl)acetyl]amino}-4-oxo-3,4-dihydrophthalazin-1-yl)methyl]carbamate

Procedure

The product of Example 41B and 2-(4,4-difluorocyclohexyl)acetic acid were treated using a method similar to that described in Example 56 to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 11.31 (s, 1H), 8.32 (dd, J=7.8, 1.4, 1H), 8.11 (d, J=8.0, 1H), 8.04-7.95 (m, 1H), 7.95-7.86 (m, 1H), 7.48-7.37 (m, 1H), 4.48-4.42 (m, 2H), 2.32-2.22 (m, 3H), 2.05-1.70 (m, 6H), 1.39 (s, 9H), 1.35-1.20 (m, 2H); MS (ESI−) M/Z 449 (M−H)−.

Sources & evidence

ORD record
ord-ebd47278ca4c4e53862464ef2827e932
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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