Triethylamine → HCID 89761782, compound

HRID 528633Notes

Reaction equation

HRID 528633 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][O:11][C:10]3[CH:14]=[C:15]([S:18](Cl)(=[O:20])=[O:19])[CH:16]=[CH:17][C:9]2=3)=[C:4]([C:22]#[N:23])[CH:3]=1.[F:24][C:25]1[C:30]([OH:31])=[C:29]([F:32])[C:28]([F:33])=[C:27]([F:34])[C:26]=1[F:35].C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][O:11][C:10]3[CH:14]=[C:15]([S:18]([O:31][C:30]4[C:29]([F:32])=[C:28]([F:33])[C:27]([F:34])=[C:26]([F:35])[C:25]=4[F:24])(=[O:20])=[O:19])[CH:16]=[CH:17][C:9]2=3)=[C:4]([C:22]#[N:23])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13041PentafluorophenolHCID 89761847HCID 89761847, compound

Product 1

HCID 89761782HCID 89761782, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(4-chloro-2-cyanophenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonyl chloride (480 mg, 1.30 mmol) in DCM (5 mL) was added pentafluorophenol (240 mg, 1.30 mmol) at 0° C. Triethylamine (0.27 mL, 1.95 mmol) was added at 0° C. and the reaction mixture was stirred at room temperature for 1 h. After completion, the reaction mixture was diluted with DCM (3 mL) and concentrated under reduced pressure. The crude mass was purified by combi flash column chromatography (12 g column; elution: 7% ethyl acetate in hexane) to provide perfluorophenyl 4-(4-chloro-2-cyanophenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonate (370 mg, 54.9%) as clear liquid. 1H NMR (400 MHz, DMSO) δ 8.22 (d, J=2.5 Hz, 1H), 7.96 (dd, J=8.7, 2.5 Hz, 1H), 7.70 (d, J=8.7 Hz, 1H), 7.38 (d, J=2.2 Hz, 1H), 7.31 (dd, J=8.7, 2.3 Hz, 1H), 6.59 (d, J=8.7 Hz, 1H), 4.41 (s, 2H), 3.86 (s, 2H); LCMS (ESI) m/z; 516.02 (M+H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude mass was purified by combi flash column chromatography (12 g column; elution: 7% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-5a4d6830661c4d4ba403f78767af9e36
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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