4-Chlorophenylacetyl chloride → Tert-butyl[(3-{[(4-chlorophenyl)acetyl]amino}-4-oxo-3,4-dihydrophthalazin-1-yl)methyl]carbamate

HRID 535502Notes

Reaction equation

HRID 535502 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].[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30](Cl)=[O:31])=[CH:25][CH: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][C:26]2[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=2)[N:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 906924-Chlorophenylacetyl chlorideHCID 131731940Tert-butyl(3-amino-4-oxo-3,4-dihydrophthalazin-1-yl)methylcarbamate

Product 1

HCID 124012735Tert-butyl[(3-{[(4-chlorophenyl)acetyl]amino}-4-oxo-3,4-dihydrophthalazin-1-yl)methyl]carbamate

Procedure

The product of Example 41B was treated with 2-(4-chlorophenyl)acetyl chloride using a method similar to that described in Example 4C to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 11.59 (s, 1H), 8.32 (dd, J=7.8, 1.4 Hz, 1H), 8.11 (ddd, J=8.0, 1.3, 0.7 Hz, 1H), 7.99 (ddd, J=8.0, 7.2, 1.5 Hz, 1H), 7.91 (ddd, J=7.8, 7.2, 1.3 Hz, 1H), 7.33-7.48 (m, 5H), 4.42-4.46 (m, 2H), 3.67 (s, 2H), 1.37 (s, 9H); MS (APCI+) M/Z 343 (M−CO2tBu+H)+.

Sources & evidence

ORD record
ord-c332989167eb4b5da38d988c08ce91e2
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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