Potassium Carbonate → HCID 67390084, compound

HRID 1020383Notes

Reaction equation

HRID 1020383 reaction equation
[N:1]1([C:7]2[O:8][C:9]([C:16]([NH:18][C:19]3[CH:20]=[C:21]4[C:26](=[CH:27][CH:28]=3)[CH2:25][NH:24][CH2:23][CH2:22]4)=[O:17])=[C:10]([C:12]([F:15])([F:14])[F:13])[N:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].I[CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38]>CC#N.CCOC(C)=O>[N:1]1([C:7]2[O:8][C:9]([C:16]([NH:18][C:19]3[CH:20]=[C:21]4[C:26](=[CH:27][CH:28]=3)[CH2:25][N:24]([CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:23][CH2:22]4)=[O:17])=[C:10]([C:12]([F:14])([F:13])[F:15])[N:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12183Ethyl iodoacetateHCID 57461816HCID 57461816, compound

Product 1

HCID 67390084HCID 67390084, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of compound 154 (0.098 g, 0.25 mmol) and K2CO3 (0.5 g) in CH3CN (5 mL) was added ethyl iodoacetate (0.036 mL). After 19 h of stirring at RT, the reaction mixture was diluted in EtOAc (50 mL) and filtered. The fitrate was washed with sat NaHCO3 (2×50 mL), dried over Na2SO4, filtered, and concentrated. The crude materials were purified by prep-TLC using 25% CH3CN in CH2Cl2 as eluents to yield compound 155 as a white solid (0.064 g, 54% yield). 1H NMR (400 MHz, DMSO-d6) δ 10.02 (s, 1H), 7.47 (d, 1H, J=2.2 Hz), 7.41 (dd, 1H, J=8.0, 2.2 Hz), 7.02 (d, 1H, J=8.4 Hz), 4.11 (q, 2H, J=7.3 Hz), 3.66 (s, 2H), 3.61 (m, 4H), 3.41 (s, 2H), 2.80 (s, 4H), 1.61 (m, 6H), 1.21 (t, 3H, J=7.3 Hz); LCMS (ESI) Rt=3.21 min, [M+1]+ 481.3.

Workup

  1. filtrationfiltered
  2. washThe fitrate was washed with sat NaHCO3 (2×50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude materials were purified

Sources & evidence

ORD record
ord-cac1bab8f3a84d73a54161de0dcabf78
Source dataset
uspto-grants-2014_05
Patent number
US08716312B2

Reaction notes

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