1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-Cyclopropyl-4-methoxy-2,6-dimethyl-N-[(4-{[4-(1-methylpiperidin-4-yl)piperazin-1-yl]carbonyl}-1,3-oxazol-2-yl)methyl]benzenesulfonamide

HRID 469062Notes

Reaction equation

HRID 469062 reaction equation
[CH:1]1([N:4]([CH2:18][C:19]2[O:20][CH:21]=[C:22]([C:24]([OH:26])=O)[N:23]=2)[S:5]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:9]=2[CH3:17])(=[O:7])=[O:6])[CH2:3][CH2:2]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:57][N:58]1[CH2:63][CH2:62][CH:61]([N:64]2[CH2:69][CH2:68][NH:67][CH2:66][CH2:65]2)[CH2:60][CH2:59]1>C(Cl)Cl>[CH:1]1([N:4]([CH2:18][C:19]2[O:20][CH:21]=[C:22]([C:24]([N:67]3[CH2:66][CH2:65][N:64]([CH:61]4[CH2:62][CH2:63][N:58]([CH3:57])[CH2:59][CH2:60]4)[CH2:69][CH2:68]3)=[O:26])[N:23]=2)[S:5]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:9]=2[CH3:17])(=[O:6])=[O:7])[CH2:2][CH2:3]1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 5663241-(1-Methyl-4-piperidinyl)piperazineHCID 583930982-({Cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-1,3-oxazole-4-carboxylic acid

Product 1

HCID 58393254N-Cyclopropyl-4-methoxy-2,6-dimethyl-N-[(4-{[4-(1-methylpiperidin-4-yl)piperazin-1-yl]carbonyl}-1,3-oxazol-2-yl)methyl]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

2-({Cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-1,3-oxazole-4-carboxylic acid (100 mg, 0.26 mmol) was dissolved in DCM (15 mL) and EDCI (70 mg, 0.36 mmol), HOBt (53 mg, 0.39 mmol) and DIPEA (0.057 mL, 0.33 mmol) were added. The resulting solution was stirred for 15 min prior to the addition of 1-(1-methylpiperidin-4-yl)piperazine (57 mg, 0.31 mmol) dissolved in DCM (2 mL) and stirred at ambient temperature for 12 h. The reaction was diluted with DCM (20 mL) and washed with water (10 mL), saturated aqueous NaHCO3 (10 mL), saturated brine (5 mL), dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by FCC with 0-2% MeOH in DCM to afford the title compound as pale yellow oil.

Workup

  1. stirringstirred at ambient temperature for 12 h
  2. washwashed with water (10 mL), saturated aqueous NaHCO3 (10 mL), saturated brine (5 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by FCC with 0-2% MeOH in DCM

Sources & evidence

ORD record
ord-948e46a6993342f38e67ceb1aa804caf
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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