Water → HCID 68532975, compound

HRID 644247Notes

Reaction equation

HRID 644247 reaction equation
[NH2:1][CH:2]([C:4]1[CH:28]=[CH:27][C:7]([C:8]([NH:10][C:11]2[CH:26]=[CH:25][CH:24]=[CH:23][C:12]=2[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=2)=[O:14])=[O:9])=[C:6]([O:29]COC)[CH:5]=1)[CH3:3].FC(F)(F)C(O)=O.O>C(Cl)Cl>[NH2:1][CH:2]([C:4]1[CH:28]=[CH:27][C:7]([C:8]([NH:10][C:11]2[CH:26]=[CH:25][CH:24]=[CH:23][C:12]=2[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=2)=[O:14])=[O:9])=[C:6]([OH:29])[CH:5]=1)[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 68535763HCID 68535763, compound

Product 1

HCID 68532975HCID 68532975, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[4-(1-aminoethyl)-2-(methoxymethoxy)benzoylamino]-N-(5-chloropyridin-2-yl)benzamide (0.205 g, 0.45 mmol) in CH2Cl2 (4.1 mL) was added trifluoroacetic acid (4.1 mL) followed by H2O (4.1 mL). The reaction was stirred at room temperature for 20-30 min. Then the volatile solvent was removed under a reduced pressure and the residue was diluted with H2O (20 mL) and carefully neutralized with solid NaHCO3. The aqueous solution was extracted with EtOAc (5×25 mL), dried (Na2 SO4) and concentrated to afford the expected product (0.180 g, 97%), TLC Rf: 0.36 (5% 2 N NH3/MeOH in CH2Cl2). 1H NMR (400 MHz, CD3OD): δ 8.44 (d, 1H, J=8.0 Hz); 8.31 (d, 1H, J=2.4 Hz); 8.23 (d, 1H, J=8.8 Hz); 7.93 (d, 1H, J=8.8 Hz); 7.86-7.82 (m, 2H); 7.59 (dt, 1H, J=2.0 and 8.8 Hz); 7.29 (dt, 1H, J=0.8 and 7.6 Hz); 7.00 (m, 2H); 4.39 (q, 1H, J=7.2 Hz); 1.58 (d, 3H, J=6.8 Hz). IS-MS (m/e): 411 (m+1) and 409 (m−1) H. Wang's Resin-linked 2-[4-(1-aminoethyl)-2-hydroxybenzoylamino]-N-(5-chloro-pyridin-2-yl)benzamide

Workup

  1. customThen the volatile solvent was removed under a reduced pressure
  2. additionthe residue was diluted with H2O (20 mL)
  3. extractionThe aqueous solution was extracted with EtOAc (5×25 mL)
  4. customdried (Na2 SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-34103903ff1d450aa63f845237b4c5f7
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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