Diisopropylethylamine → HCID 178453939, compound

HRID 573224Notes

Reaction equation

HRID 573224 reaction equation
Cl.[NH2:2][CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][CH2:5]1.F[C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH2:28])(=[O:27])=[O:26])=[CH:21][C:20]=1[N+:29]([O-:31])=[O:30].C(N(C(C)C)CC)(C)C>O1CCCC1.C(OCC)(=O)C>[N+:29]([C:20]1[CH:21]=[C:22]([S:25](=[O:27])(=[O:26])[NH2:28])[CH:23]=[CH:24][C:19]=1[NH:2][CH2:3][C@H:4]1[CH2:5][CH2:6][C@H:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])[CH2:8][CH2:9]1)([O-:31])=[O:30]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 167824874-Fluoro-3-nitrobenzenesulfonamideHCID 178453945HCID 178453945, compound

Product 1

HCID 178453939HCID 178453939, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of tert-butyl trans-4-(aminomethyl)cyclohexylcarbamate HCl (1.0 g) and 4-fluoro-3-nitrobenzenesulfonamide (0.83 g) in tetrahydrofuran (5 mL) was added diisopropylethylamine (1.98 mL) and the reaction stirred at room temperature for 1 hour. The reaction was diluted with ethyl acetate (75 mL) and washed with saturated ammonium chloride (50 mL), brine (50 mL), dried over magnesium sulfate, filtered, and concentrated. The resulting solid was triturated with dichloromethane (50 mL), filtered and dried to give the title compound.

Workup

  1. washwashed with saturated ammonium chloride (50 mL), brine (50 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting solid was triturated with dichloromethane (50 mL)
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-6d259341f0a8493b807a5e515ef28171
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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