1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58393256, compound

HRID 469015Notes

Reaction equation

HRID 469015 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:20][CH:19]=[C:18]([C:21]([OH:23])=O)[CH:17]=2)[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:24])[CH:4]=1.CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH:55]1[C@@H:59]2[CH2:60][CH2:61][CH2:62][CH2:63][C@H:58]2[N:57]=[C:56]1[C:64]1[CH:69]=[CH:68][C:67]([CH2:70][CH2:71][NH2:72])=[CH:66][CH:65]=1>CN(C=O)C>[NH:57]1[C@@H:58]2[CH2:63][CH2:62][CH2:61][CH2:60][C@H:59]2[N:55]=[C:56]1[C:64]1[CH:65]=[CH:66][C:67]([CH2:70][CH2:71][NH:72][C:21]([C:18]2[CH:17]=[C:16]([CH2:15][N:13]([S:10]([C:6]3[C:7]([CH3:9])=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[CH3:24])(=[O:11])=[O:12])[CH3:14])[O:20][CH:19]=2)=[O:23])=[CH:68][CH:69]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 583930975-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acidHCID 67329325HCID 67329325, compound

Product 1

HCID 58393256HCID 58393256, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to general procedure AG using 5-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (56 mg, 0.16 mmol), EDCI (36 mg, 0.19 mmol), HOAt (26 mg, 0.19 mmol), DIPEA (0.084 mL, 0.48 mmol) and 2-{4-[(3aR,7aR)-3a,4,5,6,7,7a-hexahydro-1H-benzimidazol-2-yl]phenyl}ethanamine (82 mg, 0.14 mmol) in DMF (1 mL). The crude product was purified using Ambersep resin, then using prep method C.

Workup

  1. customThe crude product was purified

Sources & evidence

ORD record
ord-737faed06c5d4b8d84561e47f9c033f0
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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