Tetrahydrofuran → HCID 178505299, compound

HRID 75519Notes

Reaction equation

HRID 75519 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([CH2:13][OH:14])[CH2:9][CH2:8]1)=[O:5].C1COCC1.C(N(CC)CC)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>C(Cl)Cl>[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([CH2:13][O:14][S:36]([CH3:35])(=[O:38])=[O:37])[CH2:9][CH2:8]1)=[O:5]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178523767HCID 178523767, compound2×

Product 1

HCID 178505299HCID 178505299, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Trans-2-Chloro-N-(4-hydroxymethyl-cyclohexyl)-5-trifluoromethyl-benzamide (Intermediate D, step 2) (1 g, 2.98 mmol) was suspended in DCM. THF (6 ml) was added to solubilise the alcohol. The mixture was cooled to 0° C. and treated with triethylamine (0.623 ml, 4.47 mmol) followed by dropwise addition of methanesulfonyl chloride (0.255 ml, 3.28 mmol). The reaction mixture was allowed to warm to RT stirring O/N and then diluted with DCM (50 ml). The mixture was washed with water, 1M HCl and brine. The organic portion was dried (MgSO4) and reduced under vacuum to give the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.82 (1H, s), 7.53 (1H, d), 7.45 (1H, d), 5.91 (1H, d), 4.00 (2H, d), 3.90 (1H, m), 2.94 (3H, s), 2.14 (2H, m), 1.86 (2H, m), 1.71 (1H, m), 1.19 (4H, m).

Workup

  1. temperatureto warm to RT
  2. washThe mixture was washed with water, 1M HCl and brine
  3. dry with materialThe organic portion was dried (MgSO4)

Sources & evidence

ORD record
ord-b8d3e0a248e649cc858bc5606e8791f8
Source dataset
uspto-grants-2014_09
Patent number
US08835444B2

Reaction notes

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