1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 11338457, compound

HRID 1693439Notes

Reaction equation

HRID 1693439 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([C:11]([NH:13][C@@H:14]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:15]([OH:17])=O)=[O:12])[NH:8][C:5]2=[CH:6][N:7]=1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN(C=O)C>[CH2:18]([C@H:14]([NH:13][C:11]([C:9]1[NH:8][C:5]2=[CH:6][N:7]=[C:2]([Cl:1])[CH:3]=[C:4]2[CH:10]=1)=[O:12])[C:15](=[O:17])[N:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 11382331HCID 11382331, compound

Product 1

HCID 11338457HCID 11338457, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(S)-[(5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-3-phenylpropionic acid (EXAMPLE 42, 50 mg, 0.15 mmol) in DMF (3 mL) was added pyrrolidine (13 μL, 0.16 mmol), HOBt (20 mg, 0.15 mmol) and DIPEA (51 μL, 0.29 mmol). After 5 min, EDCI (36 mg, 0.19 mmol) was added and the reaction was stirred at rt for 16 h. The solvent was removed in vacuo and the solid was triturated with water, filtered and dried to give the title compound as a beige solid. m/z (ES+)=397 [M+H]+; RT=3.38 min.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe solid was triturated with water
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-afcfbf48079d4a7995815f45eb98c9ae
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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