Aniline → HCID 11267464, compound

HRID 1693438Notes

Reaction equation

HRID 1693438 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.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN(C=O)C>[C:19]1([NH:18][C:15]([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])=[O:17])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 5

HCID 6115AnilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 11482191HCID 11482191, compound

Product 1

HCID 11267464HCID 11267464, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of [(5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]acetic acid (EXAMPLE 40, 30 mg, 0.12 mmol) in DMF (2 mL) was added aniline (12 μL, 0.13 mmol), HOBt (16 mg, 0.12 mmol) and DIPEA (41 μL, 0.24 mmol). After 5 min, EDCI (29 mg, 0.15 mmol) was added, and the reaction stirred at rt for 16 h. The solvent was removed in vacuo and the solid partitioned between water (20 mL) and ethyl acetate (3×20 mL). The combined organic fractions were dried (MgSO4), concentrated in vacuo and the residue purified by chromatography on silica gel eluting with methanol/dichloromethane (1:19) to give the title compound as a yellow solid. m/z (ES+)=329 [M+H]+; RT=3.17 min.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe solid partitioned between water (20 mL) and ethyl acetate (3×20 mL)
  3. dry with materialThe combined organic fractions were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customthe residue purified by chromatography on silica gel eluting with methanol/dichloromethane (1:19)

Sources & evidence

ORD record
ord-2d468e25f64a46aa98c79e48faa130ae
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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