Diisopropylethylamine → HCID 11199159, compound

HRID 751728Notes

Reaction equation

HRID 751728 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([C:11]([OH:13])=O)[NH:8][C:5]2=[CH:6][N:7]=1.Cl.[CH3:15][O:16][C:17](=[O:27])[C@@H:18]([NH2:26])[CH2:19][C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:15][O:16][C:17](=[O:27])[C@@H:18]([NH:26][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:13])[CH2:19][C:20]1[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 446307045-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acidHCID 67278504HCID 67278504, compound

Product 1

HCID 11199159HCID 11199159, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (Preparation 18, 185 mg, 0.94 mmol) in DMF (7 mL) was added 2-(S)-amino-3-pyridin-4-yl propionic acid methyl ester hydrochloride (Preparation 93, 204 mg, 0.94 mmol) followed by TBTU (333 mg, 1.04 mmol) and DIPEA (740 μL, 4.24 mmol), and the reaction stirred at rt for 16 h. Solvent was removed in vacuo and the residue partitioned between ethyl acetate (30 mL) and water (30 mL). The organic layer was washed with water (2×30 mL), NaHCO3 solution (3×40 mL) then brine (3×50 mL), dried (MgSO4) and the solvent removed in vacuo. Purification by chromatography (SiO2, EtOAc) gave the title compound as a pink powder. m/z (ES+)=359.11 [M+H]+; RT=2.42 min.

Workup

  1. customSolvent was removed in vacuo
  2. customthe residue partitioned between ethyl acetate (30 mL) and water (30 mL)
  3. washThe organic layer was washed with water (2×30 mL), NaHCO3 solution (3×40 mL)
  4. dry with materialbrine (3×50 mL), dried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customPurification by chromatography (SiO2, EtOAc)

Sources & evidence

ORD record
ord-f6dbff90c23646ad9e2e4aae642604df
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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