Ethyl bromoacetate → HCID 16005305, compound

HRID 348489Notes

Reaction equation

HRID 348489 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[F:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[C:19]([NH2:25])=[N:20][C:21]([SH:24])=[N:22][CH:23]=2)=[O:17])=[CH:11][CH:10]=1.C([O-])([O-])=O.[Na+].[Na+].CC#N.O>CC(C)=O>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][S:24][C:21]1[N:20]=[C:19]([NH2:25])[C:18]([C:16](=[O:17])[NH:15][C:12]2[CH:13]=[CH:14][C:9]([F:8])=[CH:10][CH:11]=2)=[CH:23][N:22]=1)[CH3:7]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 10340Sodium CarbonateHCID 18373917Acetonitrile--water (1/1)HCID 178509063HCID 178509063, compound

Product 1

HCID 16005305HCID 16005305, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of ethyl bromoacetate (0.128 g, 0.76 mmol) in acetone (2 mL) was added to a suspension of 4-amino-2-mercaptopyrimidine-5-carboxylic acid (4-fluorophenyl)amide (0.10 g, 0.38 mmol) and Na2CO3 (80 mg, 0.76 mmol) in acetone (5 mL). After stirring at ambient temperature for 2 hours, the resulting suspension was filtered and the filtrate concentrated to afford a crude solid that was recrystallized in dichloromethane/hexanes, or alternatively CH3CN/H2O) to afford the titled compound as a white solid (100 mg, 0.29 mmol, 76% yield). 1H NMR (300 MHz, d6-acetone) δ 9.60 (bs, 1H), 8.67 (s, 1H), 7.75 (m, 1H), 7.56 (m, 2H), 4.15 (m, 2H), 3.92 (s, 1H), 1.22 (m, 3H).

Workup

  1. filtrationthe resulting suspension was filtered
  2. concentrationthe filtrate concentrated
  3. customto afford a crude solid
  4. customthat was recrystallized in dichloromethane/hexanes

Sources & evidence

ORD record
ord-5812c06673994dbd82c24b91bb8f34fb
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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