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

HRID 469067Notes

Reaction equation

HRID 469067 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=CC2N(O)N=NC=2C=1.Cl.Cl.[CH3:48][NH:49][CH2:50][C:51]1[CH:62]=[CH:61][C:54]([CH2:55][N:56]2[CH2:59][CH:58]([OH:60])[CH2:57]2)=[CH:53][CH:52]=1>C(Cl)Cl>[OH:60][CH:58]1[CH2:57][N:56]([CH2:55][C:54]2[CH:61]=[CH:62][C:51]([CH2:50][N:49]([CH3:48])[C:21]([C:19]3[N:20]=[C:16]([CH2:15][N:13]([S:10]([C:6]4[C:7]([CH3:9])=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=4[CH3:24])(=[O:12])=[O:11])[CH3:14])[O:17][CH:18]=3)=[O:22])=[CH:52][CH:53]=2)[CH2:59]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 583931842-{[(4-Methoxy-2,6-dimethyl-benzenesulfonyl)-methyl-amino]-methyl}-oxazole-4-carboxylic acidHCID 672172431-{4-[(Methylamino)methyl]benzyl}azetidin-3-ol dihydrochloride

Product 1

HCID 58393374N-{4-[(3-Hydroxyazetidin-1-yl)methyl]benzyl}-2-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-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-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,3-oxazole-4-carboxylic acid (40 mg, 0.11 mmol), EDCI (29 mg, 0.15 mmol), HOBt (22 mg, 0.16 mmol) DIPEA (0.04 mL, 0.21 mmol), 1-{4-[(methylamino)methyl]benzyl}azetidin-3-ol dihydrochloride (35 mg, 0.13 mmol) and DCM (5 mL).

Sources & evidence

ORD record
ord-da11c47d37bc4301bc7f8b6d7716166b
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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