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

HRID 469074Notes

Reaction equation

HRID 469074 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.C[CH2:28][N:29]=[C:30]=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.Cl.[CH3:50][C:51]1([OH:66])[CH2:55][CH2:54][N:53]([CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[C:59](CNC)[CH:58]=2)[CH2:52]1>C(Cl)Cl>[CH:1]1([N:4]([CH2:18][C:19]2[O:20][CH:21]=[C:22]([C:24]([N:29]([CH2:30][C:60]3[CH:59]=[CH:58][C:57]([CH2:56][N:53]4[CH2:54][CH2:55][C:51]([OH:66])([CH3:50])[CH2:52]4)=[CH:62][CH:61]=3)[CH3:28])=[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])[CH2:3][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 672169773-Methyl-1-{3-[(methylamino)methyl]benzyl}pyrrolidin-3-ol dihydrochloride

Product 1

HCID 583930232-({Cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-N-{4-[(3-hydroxy-3-methylpyrrolidin-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 (24 mg, 0.12 mmol), HOBt (18 mg, 0.14 mmol) DIPEA (0.032 mL, 0.18 mmol) and 3-methyl-1-{3-[(methylamino)methyl]benzyl}pyrrolidin-3-ol dihydrochloride (30 mg, 0.10 mmol) in DCM (5 mL). The resulting residue was purified by FCC eluting with 5% MeOH in DCM to afford the title compound.

Workup

  1. customThe title compound was prepared
  2. customThe resulting residue was purified by FCC
  3. washeluting with 5% MeOH in DCM

Sources & evidence

ORD record
ord-bd677e3909b64193b289c39c801517c2
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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