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

HRID 535549Notes

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

Participants

Reactant 2

HCID 2757989Cyclohexylacetyl chloride

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

Product 1

HCID 123795492Tert-butyl({3-[(cyclohexylacetyl)amino]-4-oxo-3,4-dihydrophthalazin-1-yl}methyl)carbamate

Procedure

The product of Example 41B and 2-cyclohexylacetyl chloride were treated using a method similar to that described in Example 4C to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 11.24 (s, 1H), 8.32 (dd, J=7.8, 1.4, 1H), 8.11 (d, J=8.0, 1H), 8.03-7.94 (m, 1H), 7.90 (td, J=7.5, 1.2, 1H), 7.45-7.36 (m, 1H), 4.48-4.41 (m, 2H), 2.16 (d, J=6.7, 2H), 1.85-1.58 (m, 6H), 1.39 (s, 9H), 1.28-0.95 (m, 5H); MS (ESI−) M/Z 413 (M−H)−.

Sources & evidence

ORD record: ord-a5be1c48191b43a295c174044dadcf47
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859549B2

Reaction notes

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