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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 10146981, compound

HRID 2307723
Notes
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Reaction equation

HRID 2307723 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:40]=[CH:41][CH:42]=1)[CH2:11][N:12]([C@@H:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:33][CH2:32][CH2:31]1)[C:13]([C:15]1[CH:20]=[C:19]([C:21]([OH:23])=[O:22])[C:18]([C:24](O)=[O:25])=[CH:17][C:16]=1[C:27]([OH:29])=[O:28])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:43][O:44][C:45]1[CH:50]=[CH:49][C:48]([S:51]([NH2:54])(=[O:53])=[O:52])=[CH:47][CH:46]=1.CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.C1COCC1>[CH3:43][O:44][C:45]1[CH:46]=[CH:47][C:48]([S:51]([NH:54][C:24]([C:18]2[CH:17]=[C:16]([C:27]([OH:29])=[O:28])[C:15]([C:13]([N:12]([CH2:11][C:10]3[CH:40]=[CH:41][CH:42]=[C:8]([O:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:9]=3)[C@@H:30]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH2:33][CH2:32][CH2:31]3)=[O:14])=[CH:20][C:19]=2[C:21]([OH:23])=[O:22])=[O:25])(=[O:53])=[O:52])=[CH:49][CH:50]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 707894-MethoxybenzenesulfonamideHCID 9829395A-317491

Product 1

HCID 10146981HCID 10146981, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 8028
Tetrahydrofuran
Solvent

Procedure

The product from Example 36B (114 mg, 0.2 mmol), 4-methoxybenzenesulfonamide (37 mg, 0.2 mmol), DMAP (25 mg, 0.2 mmol), and EDCI (78 mg, 0.4 mmol) were combined in THF (10 mL) at room temperature. After stirring overnight, the mixture was concentrated under reduced pressure and CH2Cl2 (20 mL) was added. The mixture was washed with water and the organic layer concentrated under reduced pressure. The residue was purified via HPLC to provide the title compounds. 1H (500 MHz; DMSO-d6) δ6.4-8.6 (m, br., 20H) 5.0 (m, 1H) 4.7 (m, 1H) 4.1 (m, 1H) 3.5 (br, 3H) 1.4-2.7 (m, 6H); MS (M+H)+735.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure and CH2Cl2 (20 mL)
  2. additionwas added
  3. washThe mixture was washed with water
  4. concentrationthe organic layer concentrated under reduced pressure
  5. customThe residue was purified via HPLC

Sources & evidence

ORD record
ord-8fee3853e22243448830cb8e3dedd1b6
Source dataset
uspto-grants-2004_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06831193B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes