Aniline → HCID 62155529, compound

HRID 509525Notes

Reaction equation

HRID 509525 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][C:5]([Br:11])=[CH:4][N:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CS(N1C2C=CC=CC=2N=N1)(=O)=O.CCN(C(C)C)C(C)C>C1COCC1>[NH2:1][C:2]1[C:7]([C:8]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[CH:6][C:5]([Br:11])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 7374452-Amino-5-bromonicotinic acidHCID 7920441-(Methylsulfonyl)-1H-benzotriazole

Product 1

HCID 62155529HCID 62155529, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2-amino-5-bromo-pyridine-3-carboxylic acid (203 mg, 0.9354 mmol), aniline (87.11 mg, 85.23 μL, 0.9354 mmol), 1-methylsulfonylbenzotriazole (276.7 mg, 1.403 mmol) and DIPEA (241.8 mg, 325.9 μL, 1.871 mmol) in THF (2.0 mL) was heated in the microwave at 160° C. for 10 mins. The reaction mixture was concentrated and the residue partitioned between EtOAc and 2M NaOH. The organic phase was washed with brine, dried (MgSO4) and concentrated in vacuo to give the product as a yellow solid (174 mg, 64% Yield). 1H NMR (400.0 MHz, DMSO) δ 7.77 (br s, 2H), 8.18 (d, 1H) and 8.32 (d, 1H); ppm; MS (ES+) 293.94.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue partitioned between EtOAc and 2M NaOH
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-234e1a0a0f9245a6821d61b0d24857c7
Source dataset
uspto-grants-2015_08
Patent number
US09096584B2

Reaction notes

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