(Diethylamino)sulfur trifluoride → HCID 21101720, compound

HRID 1353424Notes

Reaction equation

HRID 1353424 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([NH:20][CH:21]4[CH2:26][CH2:25][CH:24](O)[CH2:23][CH2:22]4)=[O:19])[CH2:14][CH2:13]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.CCN(S(F)(F)F)CC>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([NH:20][CH:21]4[CH2:26][CH2:25][CH:24]=[CH:23][CH2:22]4)=[O:19])[CH2:14][CH2:13]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 21101951HCID 21101951, compound

Product 1

HCID 21101720HCID 21101720, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(7-chloro-4-quinolinyl)-N-(4-hydroxycyclohexyl)-1-piperazinecarboxamide (100 mg) in CH2Cl2 at −78° C. was added DAST (100 mg). The reaction was warmed to rt overnight, and quenched with NaOH (sat.). The reaction mixture was extracted with EtOAc, and dried. Concentration in vacuo followed by flash chromatography with CH2Cl2-MeOH afforded the title product. 1H NMR (DSMO-d6) 61.03 (m, 1H), 1.4 (m, 1H), 1.7 (m, 1H), 1.9 (m, 1H), 2.05 (m, 1H), 2.1 (m, 1H), 3.1 (br. s, 4H), 3.6 (br. s, 4H), 3.65 (m, 1H), 5.6 (m, 2H), 6.4 (d, 1H), 7.0 (d, 1H), 7.6 (m, 1H), 8.0 (s, 1H), 8.1 (d, 1H), 8.7 (d, 1H).

Workup

  1. customquenched with NaOH (sat.)
  2. extractionThe reaction mixture was extracted with EtOAc
  3. customdried
  4. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-432410d3c7c149f8ba2df3d669a99f45
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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