1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59753680, compound

HRID 751737Notes

Reaction equation

HRID 751737 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[Cl:15][C:16]1[N:21]=[C:20]2[NH:22][C:23]([C:25]([NH:27][C@@H:28]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)[C:29](O)=[O:30])=[O:26])=[CH:24][C:19]2=[CH:18][CH:17]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[F:39][C:36]1[CH:35]=[CH:34][C:33]([CH2:32][C@H:28]([NH:27][C:25]([C:23]2[NH:22][C:20]3=[N:21][C:16]([Cl:15])=[CH:17][CH:18]=[C:19]3[CH:24]=2)=[O:26])[C:29](=[O:30])[N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:38][CH:37]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59753690HCID 59753690, compound

Product 1

HCID 59753680HCID 59753680, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent4×

Procedure

To pyrrolidine (11.5 mg, 0.14 mmol) was added a solution of DIPEA (60 μL, 0.35 mmol) in DMF (500 μL) followed by 2-(S)-[(6-chloro-1H-pyrrolo[2,3-b]pyridine-2-carbonyl)amino]-3-(4-fluorophenyl) propionic acid (EXAMPLE 272, 50 mg, 0.14 mmol) in DMF (500 μL) and HOBt (23 mg, 0.15 mmol) in DMF (500 μL) and the mixture stirred. After 5 min EDCI (34.5 mg, 0.18 mmol) in DMF (500 μL) was added and the reaction stirred for 16 hr. Solvent was removed in vacuo then crude material purified by mass-directed purification to give the title compound. m/z (ES+)=414.93 [m+H]+; RT=3.77 min.

Workup

  1. stirringthe reaction stirred for 16 hr
  2. customSolvent was removed in vacuo
  3. customcrude material purified by mass-directed purification

Sources & evidence

ORD record
ord-1aa5113b59324ff48ef5b51172efd78b
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

Loading…