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

HRID 469073Notes

Reaction equation

HRID 469073 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.Cl.Cl.[CH3:50][NH:51][CH2:52][C:53]1[CH:66]=[CH:65][C:56]([CH2:57][N:58]2[CH2:62][CH:61]([OH:63])[CH:60]([OH:64])[CH2:59]2)=[CH:55][CH:54]=1>C(Cl)Cl>[CH:1]1([N:4]([CH2:18][C:19]2[O:20][CH:21]=[C:22]([C:24]([N:51]([CH2:52][C:53]3[CH:54]=[CH:55][C:56]([CH2:57][N:58]4[CH2:62][CH:61]([OH:63])[CH:60]([OH:64])[CH2:59]4)=[CH:65][CH:66]=3)[CH3:50])=[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])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 583930982-({Cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-1,3-oxazole-4-carboxylic acidHCID 672175101-{4-[(Methylamino)methyl]benzyl}pyrrolidine-3,4-diol dihydrochloride

Product 1

HCID 583931352-({Cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-N-{4-[(3,4-dihydroxypyrrolidin-1-yl)methyl]benzyl}-N-methyl-1,3-oxazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to general procedure BH using 2-({cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-1,3-oxazole-4-carboxylic acid (35 mg, 0.09 mmol), EDCI (25 mg, 0.13 mmol), HOBt (19 mg, 0.19 mmol) DIPEA (0.03 mL, 0.21 mmol), 1-{4-[(methylamino)methyl]benzyl}pyrrolidine-3,4-diol dihydrochloride (30 mg, 0.11 mmol) and DCM (10 mL).

Sources & evidence

ORD record
ord-d43ec0e449364a91a55e50bfffa1ab18
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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