Chloroacetyl chloride → HCID 89761950, compound

HRID 528671Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([S:21]([N:24](CC2C=CC(OC)=CC=2)[C:25]2[S:26][CH:27]=[CH:28][N:29]=2)(=[O:23])=[O:22])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=1[O:19][CH3:20].Cl[CH:40]([CH3:44])[C:41](Cl)=[O:42].ClCC(Cl)=O>>[CH3:20][O:19][C:10]1[CH:11]=[C:12]([C:15]([F:17])([F:18])[F:16])[CH:13]=[CH:14][C:9]=1[N:8]1[C:41](=[O:42])[CH:40]([CH3:44])[O:1][C:2]2[CH:3]=[C:4]([S:21]([NH:24][C:25]3[S:26][CH:27]=[CH:28][N:29]=3)(=[O:23])=[O:22])[CH:5]=[CH:6][C:7]1=2

Participants

Reactant 3

HCID 6577Chloroacetyl chloride

HCID 1110192-Chloropropionyl chloride

HCID 89761246HCID 89761246, compound

Product 1

HCID 89761950HCID 89761950, compound

Procedure

(+/−)-4-(2-methoxy-4-(trifluoromethyl)phenyl)-2-methyl-3-oxo-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide was prepared in a similar fashion to Example 223, starting from 3-hydroxy-4-((2-methoxy-4-(trifluoromethyl)phenyl)amino)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)benzenesulfonamide) (from Step 1, Example 223) and 2-chloropropanoyl chloride instead chloroacetyl chloride. Purification was achieved using reverse-phase HPLC with a Waters-Xbridge C18, 19×100 mm, 10 m column with a gradient 5-95% acetonitrile and water with 0.1% ammonium hydroxide modifier. 1H NMR (500 MHz, DMSO-d6) δ 1.53 (dd, J=16.93, 6.73 Hz, 3 H) 2.54 (s, 3 H) 3.79 (s, 1 H) 4.97-5.04 (m, 1 H) 6.40 (d, J=8.48 Hz, 1 H) 6.83 (d, J=4.58 Hz, 1H) 7.26 (d, J=4.52 Hz, 1 H) 7.30-7.42 (m, 2 H) 7.45-7.63 (m, 3 H). m/z ESI 500.0 (M+H)+.

Workup

customPurification

Sources & evidence

ORD record: ord-136c1e56125d4fbda55a76c8358cf3e8
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346798B2

Reaction notes

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