Hydrochloric Acid → HCID 67042170, compound

HRID 2047635Notes

Reaction equation

HRID 2047635 reaction equation
[Br:1][C:2]1[C:3]([N:9]([CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:10][C:11]([CH3:17])([CH3:16])[C:12]([NH:14][CH3:15])=[O:13])=[N:4][C:5](Cl)=[N:6][CH:7]=1.[NH2:23][C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][C:25]=1[O:34][CH3:35].O.Cl>CCO>[Br:1][C:2]1[C:3]([N:9]([CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:10][C:11]([CH3:17])([CH3:16])[C:12]([NH:14][CH3:15])=[O:13])=[N:4][C:5]([NH:23][C:24]2[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][C:25]=2[O:34][CH3:35])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 602411Methyl 4-amino-3-methoxybenzoateHCID 86672900HCID 86672900, compound

Product 1

HCID 67042170HCID 67042170, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

3-[(5-bromo-2-chloro-pyrimidin-4-yl)-cyclopentyl-amino]-N,2,2-trimethyl-propanamide (266 mg, 0.6825 mmol) and methyl 4-amino-3-methoxy-benzoate (185.5 mg, 1.024 mmol) were dissolved in EtOH (2 mL) and Water (8 mL) and treated with HCl (134.5 μL of 37% w/v, 1.365 mmol). Heat at 90° C. overnight. Cool to ambient temperature and remove solvent in vacuo. The reaction mixture was diluted with EtOAc/NaHCO3 and extracted with EtOAc. The combined organic extracts were dried (Na2SO4), filter and concentrated. The crude residue was purified by column chromatography (0 to 100% EtOAc/Petrol) to give the sub-title compound as a beige oil (84 mg, 23%); NMR (400.0 MHz, DMSO) d 0.97 (s, 6H), 1.44-1.69 (m, 8H), 2.45 (d; J=4.4 Hz, 3H), 3.58 (br s, 2H), 3.84 (s, 3H), 3.96 (s, 3H), 4.11 (quin, 1H), 7.32-7.34 (m, 1H), 7.52 (d, J=1.8 Hz, 1H), 7.61 (d, 1H), 8.07 (s, 1H), 8.38 (s, 1H) and 8.43 (d, J=8.5 Hz, 1H); MS ES(+) 536.0, ES (−) 534.1.

Workup

  1. temperatureCool to ambient temperature
  2. customremove solvent in vacuo
  3. additionThe reaction mixture was diluted with EtOAc/NaHCO3
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. filtrationfilter
  7. concentrationconcentrated
  8. customThe crude residue was purified by column chromatography (0 to 100% EtOAc/Petrol)

Sources & evidence

ORD record
ord-be09b67fc1944b57b30d0f9c28e2288f
Source dataset
uspto-grants-2013_11
Patent number
US08592577B2

Reaction notes

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