4-Chlorophenylacetyl chloride → HCID 70976263, compound

HRID 535628Notes

Reaction equation

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

Participants

Reactant 2

HCID 906924-Chlorophenylacetyl chloride

HCID 70976060HCID 70976060, compound

Product 1

HCID 70976263HCID 70976263, compound

Procedure

The product from Example 220B and (4-chlorophenyl)acetyl chloride were processed using a method similar to that described in Example 4C to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.48 (s, 1H), 8.29 (dd, J=7.8, 1.2 Hz, 1H), 7.96-8.03 (m, 2H), 7.90 (ddd, J=7.9, 6.7, 1.4 Hz, 1H), 7.40-7.41 (m, 4H), 3.91 (dd, J=11.1, 2.6 Hz, 1H), 3.79 (td, J=11.4, 2.3 Hz, 1H), 3.67 (s, 2H), 3.56-3.65 (m, 1H), 3.26-3.32 (m, 2H), 2.76-2.84 (m, 1H), 2.51-2.57 (m, 1H), 1.48 (p, J=7.1 Hz, 2H), 0.92 (t, J=7.4 Hz, 3H); MS (DCI+) M/Z 427 (M+H)+, 444 (M+NH4)+.

Sources & evidence

ORD record: ord-25824dcb3e64476f9bca282ce780bd2f
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859549B2

Reaction notes

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