Ethanol → HCID 67401491, compound

HRID 711901Notes

Reaction equation

HRID 711901 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C@@H:11]2[CH2:15][CH2:14][CH2:13][C@H:12]2[CH3:16])[C:3]=1[C:4]#[N:5].[S:17](Cl)(=[O:20])(=[O:19])[NH2:18].C(O)C.[OH-].[Na+]>CC(N(C)C)=O.C(OCC)(=O)C>[NH2:5][C:4]1[C:3]2[C:6]([O:10][C@@H:11]3[CH2:15][CH2:14][CH2:13][C@H:12]3[CH3:16])=[CH:7][CH:8]=[CH:9][C:2]=2[NH:1][S:17](=[O:20])(=[O:19])[N:18]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 24499Chlorosulfamic acidHCID 66746534HCID 66746534, compound

Product 1

HCID 67401491HCID 67401491, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 2-amino-6-(trans-2-methylcyclopentyloxy)benzonitrile (Example 264a) (150 mg, 0.694 mmol) in dimethylacetamide (3 mL) under N2 was added sulfamoyl chloride (3 equiv.). The reaction mixture was stirred at room temperature under N2 for 2 hours, diluted with ethyl acetate (50 mL) and quenched with water (20 mL). The layers were separated. The organic extract was evaporated. Ethanol (3 mL) and aqueous NaOH (2N, 2.5 equiv.) were consecutively added to the residue. The resulting mixture was heated at 90° C. for 16 hours. The workup was performed as in Example 111 to provide the desired product (160 mg, 78%) as a white powder. 1H NMR (400 MHz, DMSO-d6) δ 1.02 (d, J=6.4 Hz, 3H), 1.26 (m, 1H), 1.71 (br s, 3H), 1.89 (m, 1H), 2.12 (m, 1H), 2.24 (m, 1H), 4.55 (br s, 1H), 6.60 (d, J=8.0 Hz, 1H), 6.71 (d, J=8.0 Hz, 1H), 7.45 (t, J=8.0 Hz, 1H), 7.73 (br s, 1H), 8.35 (br s, 1H), 10.96 (br s, 1H). MS 296 (MH+).

Workup

  1. customquenched with water (20 mL)
  2. customThe layers were separated
  3. extractionThe organic extract
  4. customwas evaporated
  5. temperatureThe resulting mixture was heated at 90° C. for 16 hours

Sources & evidence

ORD record
ord-86eb60158a934b9c916d6eeb3ed277b5
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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