4-Toluenesulfonyl chloride → HCID 12041755, compound

HRID 1263633Notes

Reaction equation

HRID 1263633 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[NH:4][C:5]2[C:6]([N:17]=1)=[C:7]1[C:12](=[CH:13][CH:14]=2)[CH2:11][CH2:10][CH:9]([CH2:15][OH:16])[O:8]1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>N1C=CC=CC=1.C(OCC)(=O)C>[F:19][C:2]([F:1])([F:18])[C:3]1[NH:4][C:5]2[C:6]([N:17]=1)=[C:7]1[C:12](=[CH:13][CH:14]=2)[CH2:11][CH2:10][CH:9]([CH2:15][O:16][S:26]([C:23]2[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=2)(=[O:28])=[O:27])[O:8]1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 12041754HCID 12041754, compound

Product 1

HCID 12041755HCID 12041755, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (2-trifluoromethyl-3,6,7,8-tetrahydro-9-oxa-1,3-diaza-cyclopenta[a]naphthalen-8-yl)-methanol (400 mg, 1.47 mmol) and p-toluenesulfonyl chloride (344 mg, 1.76 mmol) in anhydrous pyridine (50 mL) was stirred for 12 hours and then the solvent was removed in vacuo to give a residue. The residue was dissolved in ethyl acetate (100 mL) and washed with water (3×30 mL). The organic layer was dried over anhydrous Na2SO4, filtered, and the solvent removed in vacuo to a residue. The residue was purified by chromatography (20% CH2Cl2-hexanes) to give 545 mg (87%) of the title compound as a solid: mp 160° C.; 1H NMR (400 MHz, CDCl3): [tautamer a]:δ1.95 (m, 1H), 2.05 (m, 1H), 2.44 (s, 3H), 2.90 (m, 2H), 4.30 (m, 2H), 4.40 (m, 1H), 7.02 (d, J=8.1 Hz, 1H), 7.32 (d, J=8.1 Hz, 1H), 7.35 (d, J=8.3 Hz, 2H), 7.83 (d, J=8.3 Hz, 2H), 10.35 (bs, 1H). [tautamer b]: δ1.95 (m, 1H), 2.05 (m, 1H), 2.44 (s, 3H), 2.90 (m, 2H), 4.25 (m, 2H), 4.40 (m, 1H), 7.02 (d, J=8.1 Hz, 1H), 7.08 (d, J=8.1 Hz, 1H), 7.34 (d, J=8.3 Hz, 2H), 7.84 (d, J=8.3 Hz, 2H), 9.95 (bs, 1H); IR: 3400, 3080, 2970, 1600, 1550, 1500, 1080 cm−1; MS 427 [M+H]+.

Workup

  1. customthe solvent was removed in vacuo
  2. customto give a residue
  3. washwashed with water (3×30 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customthe solvent removed in vacuo to a residue
  7. customThe residue was purified by chromatography (20% CH2Cl2-hexanes)

Sources & evidence

ORD record
ord-b0ab8d0aa0a142bca1138e6d954574b0
Source dataset
uspto-grants-2003_04
Patent number
US06541502B1

Reaction notes

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