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

HRID 469061Notes

Reaction equation

HRID 469061 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[N:5]=[C:6]([CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[S:7][CH:8]=1.[CH:15]1([N:18]([CH2:32][C:33]2[O:34][CH:35]=[C:36]([C:38]([OH:40])=O)[N:37]=2)[S:19]([C:22]2[C:27]([CH3:28])=[CH:26][C:25]([O:29][CH3:30])=[CH:24][C:23]=2[CH3:31])(=[O:21])=[O:20])[CH2:17][CH2:16]1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O>CN(C=O)C>[CH:15]1([N:18]([CH2:32][C:33]2[O:34][CH:35]=[C:36]([C:38]([N:2]([CH3:1])[CH2:3][C:4]3[N:5]=[C:6]([CH2:9][N:10]4[CH2:14][CH2:13][CH2:12][CH2:11]4)[S:7][CH:8]=3)=[O:40])[N:37]=2)[S:19]([C:22]2[C:23]([CH3:31])=[CH:24][C:25]([O:29][CH3:30])=[CH:26][C:27]=2[CH3:28])(=[O:21])=[O:20])[CH2:17][CH2:16]1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 46785587N-methyl-1-[2-(pyrrolidin-1-ylmethyl)-1,3-thiazol-4-yl]methanamineHCID 583930982-({Cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-1,3-oxazole-4-carboxylic acid

Product 1

HCID 583933672-({Cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-N-methyl-N-{[2-(pyrrolidin-1-ylmethyl)-1,3-thiazol-4-yl]methyl}-1,3-oxazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to general procedure AH using N-methyl-1-[2-(pyrrolidin-1-ylmethyl)-1,3-thiazol-4-yl]methanamine (40 mg, 189 μmol), 2-({cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-1,3-oxazole-4-carboxylic acid (72 mg, 189 μmol), DIPEA (0.1 mL, 575 μmol), EDCI (72 mg, 378 μmol), HOBt monohydrate (58 mg, 378 μmol) and DMF (1.5 mL). The resulting crude compound was purified by FCC eluting with 99:1 DCM:7N NH3 in MeOH.

Workup

  1. customThe resulting crude compound was purified by FCC
  2. washeluting with 99:1 DCM

Sources & evidence

ORD record
ord-279c2212368149ae9bef432626d7388c
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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