1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-({Cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-N-(2-piperidin-3-ylethyl)-1,3-oxazole-4-carboxamide

HRID 469060Notes

Reaction equation

HRID 469060 reaction equation
[CH:1]1([N:4]([CH2:18][C:19]2[O:20][CH:21]=[C:22]([C:24](O)=[O:25])[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=C2N=NN(O)C2=CC=1.O.CCN(C(C)C)C(C)C.[NH2:58][CH2:59][CH2:60][CH:61]1[CH2:66][CH2:65][CH2:64][N:63]([C:67]([O:69][C:70]([CH3:73])([CH3:72])[CH3:71])=[O:68])[CH2:62]1>CN(C=O)C>[CH:1]1([N:4]([CH2:18][C:19]2[O:20][CH:21]=[C:22]([C:24]([NH:58][CH2:59][CH2:60][CH:61]3[CH2:66][CH2:65][CH2:64][NH:63][CH2:62]3)=[O:25])[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.[CH:1]1([N:4]([CH2:18][C:19]2[O:20][CH:21]=[C:22]([C:24]([NH:58][CH2:59][CH2:60][CH:61]3[CH2:66][CH2:65][CH2:64][N:63]([C:67]([O:69][C:70]([CH3:73])([CH3:72])[CH3:71])=[O:68])[CH2:62]3)=[O:25])[N:23]=2)[S:5]([C:8]2[C:9]([CH3:17])=[CH:10][C:11]([O:15][CH3:16])=[CH:12][C:13]=2[CH3:14])(=[O:6])=[O:7])[CH2:2][CH2:3]1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 5001227Tert-butyl 3-(2-aminoethyl)piperidine-1-carboxylateHCID 583930982-({Cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-1,3-oxazole-4-carboxylic acid

Product 2

HCID 461759082-({Cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-N-(2-piperidin-3-ylethyl)-1,3-oxazole-4-carboxamideHCID 67328832Tert-butyl 3-[2-({[2-({cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-1,3-oxazol-4-yl]carbonyl}amino)ethyl]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to general procedure AH using 2-({cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-1,3-oxazole-4-carboxylic acid (38 mg, 100 mop, EDCI (23 mg, 120 mop, HOBt monohydrate (18 mg, 120 μmol), DIPEA (69 μL, 400 mol), tert-butyl 3-(2-aminoethyl)piperidine-1-carboxylate (23 mg, 100 μmol) and DMF (750 L). The resulting crude compound was purified by FCC eluting with 100% EtOAc to afford tert-butyl 3-[2-({[2-({cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-1,3-oxazol-4-yl]carbonyl}amino)ethyl]piperidine-1-carboxylate. Yield: 38 mg, 64%.

Workup

  1. customThe resulting crude compound was purified by FCC
  2. washeluting with 100% EtOAc

Sources & evidence

ORD record
ord-c7eeac8c0c384b4f8cfbf505a0051400
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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