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

HRID 469032Notes

Reaction equation

HRID 469032 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]([CH2:15][C:16]2[O:17][CH:18]=[C:19]([C:21](O)=[O:22])[N:20]=2)[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:24])[CH:4]=1.CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1.[CH3:46][N:47]1[CH2:52][CH2:51][CH:50]([N:53]2[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]2)[CH2:49][CH2:48]1>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]([CH3:14])[CH2:15][C:16]2[O:17][CH:18]=[C:19]([C:21]([N:56]3[CH2:55][CH2:54][N:53]([CH:50]4[CH2:51][CH2:52][N:47]([CH3:46])[CH2:48][CH2:49]4)[CH2:58][CH2:57]3)=[O:22])[N:20]=2)(=[O:11])=[O:12])=[C:5]([CH3:24])[CH:4]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 5663241-(1-Methyl-4-piperidinyl)piperazineHCID 583931842-{[(4-Methoxy-2,6-dimethyl-benzenesulfonyl)-methyl-amino]-methyl}-oxazole-4-carboxylic acid

Product 1

HCID 583934034-Methoxy-N,2,6-trimethyl-N-[(4-{[4-(1-methylpiperidin-4-yl)piperazin-1-yl]carbonyl}-1,3-oxazol-2-yl)methyl]benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,3-oxazole-4-carboxylic acid (50 mg, 0.14 mmol) was dissolved in DMF (3 mL) and EDCI (32 mg, 0.17 mmol) and HOAt (23 mg, 0.17 mmol) were added. The resulting solution was stirred for 60 min at ambient temperature prior to the addition of a solution of 1-(1-methylpiperidin-4-yl)piperazine (31 mg, 0.17 mmol) in DMF (2 mL) and the reaction stirred at ambient temperature for 18 h. The reaction was diluted with EtOAc (20 mL) and washed with water (2×5 mL), saturated brine (5 mL), dried over Na2SO4 and concentrated in vacuo. The resulting oil was purified using FCC, eluting with 10% MeOH in DCM, to afford the title compound.

Workup

  1. stirringthe reaction stirred at ambient temperature for 18 h
  2. washwashed with water (2×5 mL), saturated brine (5 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting oil was purified
  6. washeluting with 10% MeOH in DCM

Sources & evidence

ORD record
ord-aa0b854fc860484784ac3a84717e0c61
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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