1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 11415611, compound

HRID 1693451Notes

Reaction equation

HRID 1693451 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([C:11]([NH:13][CH2:14][C:15]([OH:17])=O)=[O:12])[NH:8][C:5]2=[CH:6][N:7]=1.Cl.[OH:19][CH:20]1[CH2:23][NH:22][CH2:21]1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN(C=O)C>[OH:19][CH:20]1[CH2:23][N:22]([C:15](=[O:17])[CH2:14][NH:13][C:11]([C:9]2[NH:8][C:5]3=[CH:6][N:7]=[C:2]([Cl:1])[CH:3]=[C:4]3[CH:10]=2)=[O:12])[CH2:21]1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27592903-Hydroxyazetidine hydrochlorideHCID 11482191HCID 11482191, compound

Product 1

HCID 11415611HCID 11415611, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[(5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]acetic acid (30 mg, 0.12 mmol), 3-hydroxyazetidine hydrochloride (13 mg, 0.12 mmol) and HOBt (16 mg, 0.12 mmol) were dissolved in DMF (3 ml) and DIPEA (4311, 0.25 mmol). After 5 min, EDCI (30 mg, 0.15 mmol) was added and the reaction mixture stirred at rt for 16 h. The solvent was removed in vacuo and the residue partitioned between water (20 ml) and DCM (3×20 ml). The combined organics were dried (MgSO4), concentrated in vacuo and the residue purified by chromatography on silica gel eluting with methanol:dichloromethane (1:24) to give the title compound as a white solid. δH (CD3OD): 4.06-4.15 (3H, m), 4.40-4.46 (1H, m), 4.55-4.63 (1H, m), 4.77-4.94 (2H, m), 7.14 (1H, s), 7.71 (1H, s), 8.62 (1H, s); RT=2.82 min.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between water (20 ml) and DCM (3×20 ml)
  3. dry with materialThe combined organics were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customthe residue purified by chromatography on silica gel eluting with methanol:dichloromethane (1:24)

Sources & evidence

ORD record
ord-c4da3dcc8a724e43b3197cf928d8b675
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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