Chlorosulfamic acid → HCID 66747247, compound

HRID 711777Notes

Reaction equation

HRID 711777 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][C@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17](=[O:21])[CH2:18][CH2:19][CH3:20])[C:3]=1[C:4]#[N:5].[S:22](Cl)(=[O:25])(=[O:24])[NH2:23]>C(#N)C>[NH2:5][C:4]1[C:3]2[C:6]([O:10][CH2:11][C@H:12]3[CH2:16][CH2:15][CH2:14][N:13]3[C:17](=[O:21])[CH2:18][CH2:19][CH3:20])=[CH:7][CH:8]=[CH:9][C:2]=2[NH:1][S:22](=[O:25])(=[O:24])[N:23]=1

Participants

4

Reactant 2

HCID 24499Chlorosulfamic acidHCID 66745702HCID 66745702, compound

Product 1

HCID 66747247HCID 66747247, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (R)-2-amino-6-((1-butyrylpyrrolidin-2-yl)methoxy)benzonitrile (84 mg, 0.29 mmol) (Example 176a) in acetonitrile (9 mL), was added sulfamoyl chloride (70 mg, 0.60 mmol). The reaction was stirred at rt for 20 h, and upon completion was concentrated in vacuo. The resulting residue was dissolved in EtOH (1 mL), and 2N aqueous NaOH (4 mL) was added. The mixture was refluxed for 2 h, and upon completion was cooled to rt, neutralized with 1N HCl and stirred at 0° C. The resulting precipitate was collected by vacuum filtration to provide the desired product (38 mg, 35%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 0.89 (t, J=7.3 Hz, 3H), 1.54 (sext, J=7.3 Hz, 2H), 1.94 (m, 4H), 2.26 (t, J=7.3 Hz, 2H), 3.49 (m, 2H), 4.10 (m, 1H), 4.25 (m, 1H), 4.43 (m, 1H), 6.62 (d, J=8.2 Hz, 1H), 6.90 (d, J=8.2 Hz, 1H), 7.45 (t, J=8.2 Hz, 1H), 8.08 (br s, 1H), 8.34 (br s, 1H), 10.93 (br s, 1H). MS 367 (MH+).

Workup

  1. concentrationupon completion was concentrated in vacuo
  2. dissolutionThe resulting residue was dissolved in EtOH (1 mL)
  3. addition2N aqueous NaOH (4 mL) was added
  4. temperatureThe mixture was refluxed for 2 h
  5. temperatureupon completion was cooled to rt
  6. stirringstirred at 0° C
  7. filtrationThe resulting precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-daf1419a34fd44258aeea30dc10e6a9c
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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