Aniline → HCID 58674485, compound

HRID 1994133Notes

Reaction equation

HRID 1994133 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([OH:22])=O)=[CH:14][CH:13]=2)[CH:8]=[CH:7][N:6]=1)=[O:4].[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl.O>[NH:23]([C:20](=[O:22])[CH2:19][CH2:18][C:15]1[CH:14]=[CH:13][C:12]([O:11][C:9]2[CH:8]=[CH:7][N:6]=[C:5]([C:3]([NH:2][CH3:1])=[O:4])[CH:10]=2)=[CH:17][CH:16]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 58674341HCID 58674341, compound

Product 1

HCID 58674485HCID 58674485, compoundYield 36.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(4-(2-(methylcarbamoyl)pyridin-4-yloxy)phenyl)-propanoic acid (100 mg, 0.33 mmol), aniline (0.033 mL, 0.36 mmol), and TBTU (117 mg, 0.36 mmol) in DCM (5 mL) was stirred at rt. To this slurry was added DIPEA (0.20 mL, 1.16 mmol). The mixture was allowed to stir at rt overnight and then diluted with water. The aqueous phase was separated and extracted with DCM. The organic solutions were combined, washed with brine, dried over MgSO4, filtered, and concentrated. The resulting solid was treated with MeOH and filtered to give 45 mg of a white solid. 1H NMR (400 MHz, d6-DMSO) δ: 9.90 (br s, 1H), 8.71-8.78 (m, 1H), 8.48 (d, J=5.6 Hz, 1H), 7.55-7.60 (m, 2H), 7.36-7.40 (m, 2H), 7.36 (d, J=2.4 Hz, 1H), 7.25-7.31 (m, 2H), 7.12-7.16 (m, 2H), 7.11 (dd, J=5.2, 2.4 Hz, 1H), 6.99-7.04 (m, 1H), 2.93-2.98 (m, 2H), 2.77 (d, J=4.8 Hz, 3H), and 2.64-2.69 (m, 2H).

Workup

  1. stirringto stir at rt overnight
  2. customThe aqueous phase was separated
  3. extractionextracted with DCM
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. additionThe resulting solid was treated with MeOH
  9. filtrationfiltered

Sources & evidence

ORD record
ord-d0e28ebafd1d4e8f98c53a656404bf0f
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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