HCID 68675774, compound → HCID 68674916, compound

HRID 1993074Notes

Reaction equation

HRID 1993074 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH:7]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[CH:23]=[C:24]([C:28]4[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=4)[CH:25]=[CH:26][CH:27]=3)=[CH:16][CH:15]=2)[CH2:8][C:9]([O:11]CC)=[O:10])[S:5][CH:6]=1>CO.C1COCC1.O>[CH3:1][C:2]1[N:3]=[C:4]([CH:7]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:21][C:22]3[CH:23]=[C:24]([C:28]4[CH:29]=[CH:30][C:31]([C:34]([F:37])([F:35])[F:36])=[CH:32][CH:33]=4)[CH:25]=[CH:26][CH:27]=3)=[CH:18][CH:19]=2)[CH2:8][C:9]([OH:11])=[O:10])[S:5][CH:6]=1

Participants

3

Reactant 1

HCID 68675774HCID 68675774, compound

Product 1

HCID 68674916HCID 68674916, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Compound 51.3 (50 mg, 0.1 mmol) was dissolved in MeOH/THF/H2O (1:1:1, 3 mL). The resulting mixture was stirred at room temperature for 2 h. The reaction mixture was acidified to PH=4 and extracted with dichloromethane (3 mL×3). The product was purified on reverse phase HPLC to yield compound 51 (40 mg). MS ESI (pos.) m/e: 498 (M+H). 1H NMR (400 MHz) (DMSO) δ 7.92 (2H, d, J=8.1 Hz); 7.84 (3H, d, J=8.8 Hz); 7.71 (1H, t, J=5.1 Hz); 7.54 (2H, d, J=7 Hz); 7.29 (2H, d, J=8.7 Hz); 7.09 (1H, s); 7.01 (2H, d, J=8.7 Hz); 5.18 (2H, s); 4.66 (1H, m); 3.2 (1H, m); 2.93 (1H, m); 2.33 (3H, s).

Workup

  1. extractionextracted with dichloromethane (3 mL×3)
  2. customThe product was purified on reverse phase HPLC

Sources & evidence

ORD record
ord-341945ba4ce3453081e0f517a58f3f1f
Source dataset
uspto-grants-2010_01
Patent number
US07649110B2

Reaction notes

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