Water → HCID 178506260, compound

HRID 1263637Notes

Reaction equation

HRID 1263637 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[NH:4][C:5]2[C:6]([N:27]=1)=[C:7]1[C:12](=[CH:13][CH:14]=2)[CH2:11][CH2:10][CH:9]([CH2:15]OS(C2C=CC(C)=CC=2)(=O)=O)[O:8]1.[CH2:30]([NH2:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.O>CS(C)=O>[CH2:30]([NH:37][CH2:15][CH:9]1[O:8][C:7]2[C:12](=[CH:13][CH:14]=[C:5]3[N:4]=[C:3]([C:2]([F:29])([F:28])[F:1])[NH:27][C:6]3=2)[CH2:11][CH2:10]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7504BenzylamineHCID 12041755HCID 12041755, compound

Product 1

HCID 178506260HCID 178506260, compoundYield 173.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of toluene-4-sulfonic acid 2-trifluoromethyl-3,6,7,8-tetrahydro-9-oxa-1,3-diaza-cyclopenta[a]naphthalen-8-ylmethyl ester (213 mg, 0.5 mmol) in dimethyl sulfoxide (20 mL) was added benzylamine (268 mg, 2.5 mmol). The reaction mixture was stirred at 80° C. for 6 h, cooled to room temperature and then poured into water (20 mL), extracted with chloroform (3×30 mL) dried over anhydrous Na2SO4. Purification by chromatography (ethyl acetate) provided 314 mg (87%) of the title compound which was converted to its oxalate salt: mp 244° C.; 1H NMR (400 MHz, CDCl3): δ1.81 (m, 1H), 2.13 (m, 1H), 2.84 (m, 2H), 3.28 (m, 2H), 4.25 (d, J=13.4 Hz, 1H), 4.31 (d, J=13.4 Hz, 1H), 4.50 (m, 1H), 7.08 (d, J=8.4 Hz, 1H), 7.17 (d, J=8.4 Hz, 1H), 7.42 (m, 3H), 7.58 (m, 2H), 13.85 (bs, 1H); IR: 3450, 3080, 2980, 1725, 1640, 1600, 1550,1080 cm−1; MS 362 [M+H]+.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with chloroform (3×30 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. customPurification by chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-220c674aa8634056b7b24db79c85d519
Source dataset
uspto-grants-2003_04
Patent number
US06541502B1

Reaction notes

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