Dimethylamine → HCID 59432814, compound

HRID 1893845Notes

Reaction equation

HRID 1893845 reaction equation
[C:1]([C@H:4]([N:9]([CH2:20][C:21]1[CH:32]=[CH:31][C:24]([CH2:25]OS(C)(=O)=O)=[CH:23][CH:22]=1)[S:10]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[CH2:5][CH:6]([CH3:8])[CH3:7])(=[O:3])[NH2:2].C[CH2:34][N:35](CC)[CH2:36]C.CNC>C(Cl)Cl>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([S:10]([N:9]([C@H:4]([CH2:5][CH:6]([CH3:7])[CH3:8])[C:1]([NH2:2])=[O:3])[CH2:20][C:21]2[CH:22]=[CH:23][C:24]([CH2:25][N:35]([CH3:36])[CH3:34])=[CH:31][CH:32]=2)(=[O:12])=[O:11])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8471TriethylamineHCID 59001047HCID 59001047, compound

Product 1

HCID 59432814HCID 59432814, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of methanesulfonic acid 4-{[N-((1R)-1-carbamoyl-3-methyl-butyl)-N-(4-chlorobenzenesulfonyl)amino]-methyl}-benzyl ester (150 mg, 0.298 mmol) in (3 mL) CH2Cl2 at 0° C. was added 1 equivalent of Et3N, followed by dimethylamine (0.3 mL, 2 M in THF). The reaction was stirred overnight at rt. The mixture was diluted with CH2Cl2, washed with H2O, brine, dried over MgSO4, and concentrated to give an amber glass. Purification by flash chromatography (SiO2, 10% MeOH/CH2Cl2) afforded the title compound (95 mg) in 71% yield. MS (ESI), (M+H)+452.23, 1H NMR (CDCl3) δ 7.94 (d, 2H, J=8.0), 7.74 (d, 2H, J=8.0), 7.63 (d, 2H, J=8.0) 7.38 (d, 2H, J=8.0), 6.23 (br s, 1H), 5.35 (br s, 1H), 4.22 (d, 1H, Jab=16), 4.14 (d, 1H, Jab=16), 3.28-3.23 (m, 3H), 2.17 (br s, 6H), 1.95 (m, 1H), 1.55 (m, 2H), 0.96 (d, 3H, J=7.0), 0.93 (d, 3H, J=7.0).

Workup

  1. washwashed with H2O, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customto give an amber glass
  5. customPurification by flash chromatography (SiO2, 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-46ac683d6b614580b74d571cb2768f31
Source dataset
uspto-grants-2013_08
Patent number
US08513253B2

Reaction notes

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