Triethylamine → 4-[2-Amino-6-(5-bromo-2-ethoxy-phenyl)-pyrimidin-4-ylamino]-N-hydroxy-benzamide

HRID 28658Notes

Reaction equation

HRID 28658 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:18]2[CH:23]=[C:22]([Br:24])[CH:21]=[CH:20][C:19]=2[O:25][CH2:26][CH3:27])[N:3]=1.[N:28]1([OH:37])C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.Cl.NO.C(N(CC)CC)C>CN(C)C=O>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([NH:28][OH:37])=[O:14])=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:18]2[CH:23]=[C:22]([Br:24])[CH:21]=[CH:20][C:19]=2[O:25][CH2:26][CH3:27])[N:3]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 443297Hydroxyamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 443138224-[2-Amino-6-(5-bromo-2-ethoxy-phenyl)-pyrimidin-4-ylamino]-benzoic acid

Product 1

HCID 426067584-[2-Amino-6-(5-bromo-2-ethoxy-phenyl)-pyrimidin-4-ylamino]-N-hydroxy-benzamideYield 73.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-[2-amino-6-(5-bromo-2-ethoxy-phenyl)-pyrimidin-4-ylamino]-benzoic acid (0.086 g, 0.20 mmol) in dimethylformamide (3.0 ml) was added benzotriazol-1-ol (0.054 g, 0.40 mmol) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.086 g, 0.44 mmol). After stirring at room temperature for 1 hour, hydroxylamine hydrochloride (0.070 g, 1.0 mmol) was added followed by triethylamine (0.1 g, 1.0 mmol). After stirring for 16 hours, the solvent was evaporated under reduced pressure and the residue was treated with 1 M aqueous sodium carbonate solution (10 ml). Filtration provided the title compound (0.065 g, 73% yield) as a light brown solid. 1H NMR (DMSO-d6) δ 1.38 (t, 3H, J=6.9 Hz, CH3), 4.12 (q, 2H, J=6.9 Hz, CH2), 6.32 (s, 2H, NH2), 6.79 (s, 1H, Ar), 7.08 (d, 1H, J=8.9 Hz, Ar), 7.52 (dd, 1H, J=8.9 Hz, J=2.6 Hz, Ar), 7.66 (b, 4H, Ar), 8.04 (d, 1H, J=2.6 Hz, Ar), 9.24 (s, 1H, NH).

Workup

  1. stirringAfter stirring for 16 hours
  2. customthe solvent was evaporated under reduced pressure
  3. additionthe residue was treated with 1 M aqueous sodium carbonate solution (10 ml)
  4. filtrationFiltration

Sources & evidence

ORD record
ord-be57e1dce42d4e4c850cb7e962f6d289
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Reaction notes

Loading…