Diisopropylethylamine → HCID 178453939, compound

HRID 1043244Notes

Reaction equation

HRID 1043244 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-be8e5d0c957a468f95eb3a5bc8d5031c
Source dataset
uspto-grants-2013_10
Patent number
US08557983B2

Reaction notes

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