Phenylacetyl chloride → HCID 67242588, compound

HRID 2422111Notes

Reaction equation

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

Participants

Reactant 2

HCID 7679Phenylacetyl chloride

HCID 67241221HCID 67241221, compound

Product 1

HCID 67242588HCID 67242588, compoundYield 78%

Procedure

The title compound was prepared as described for Example 105 from phenylacetic chloride and 2-tert-butyl-5-phenyl-4-(piperidin-4-ylamino)isothiazol-3(2H)-one 1,1-dioxide (Example 75) to give the title compound (0.103 g, 78%). 1H NMR (500 MHz CDCl3): δ 7.54-7.47 (m, 2H), 7.47-7.41 (m, 3H), 7.34-7.29 (m, 2H), 7.27-7.23 (m, 1H), 7.18 (d, 2H), 5.12 (d, 1H), 4.43-4.26 (m, 1H), 3.70-3.61 (m, 3H), 3.11-3.02 (m, 1H), 2.55-2.47 (m, 1H), 2.28-2.20 (m, 1H), 1.90-1.65 (m, 11H), 1.54-1.47 (m, 1H), 1.19 (dq, 1H), 0.91 (dq, 1H); 13C δ NMR (125 MHz CDCl3): 169.5, 159.7, 135.0, 133.9, 131.8, 130.2, 129.0, 128.9, 128.6, 127.2, 125.2, 107.5, 61.9, 50.2, 44.6, 41.3, 41.2, 40.4, 32.6, 32.1, 27.8; Mass Spectrum: M+H+ 482.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-79fa353fc01f4eb197a8aac60ff11d32
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960380B2

Reaction notes

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