Methyl Acrylate → Methyl 3-(1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)cyclopropylamino)propanoate

HRID 1177462Notes

Reaction equation

HRID 1177462 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:26]2([NH2:29])[CH2:28][CH2:27]2)[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.[C:30]([O:34][CH3:35])(=[O:33])[CH:31]=[CH2:32]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:26]2([NH:29][CH2:32][CH2:31][C:30]([O:34][CH3:35])=[O:33])[CH2:28][CH2:27]2)[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:18][CH2:19]1)[N:11]=2

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 446011061-(3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)cyclopropanamine

Product 1

HCID 68635658Methyl 3-(1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)cyclopropylamino)propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

1-(3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)-cyclopropanamine (0.067 g, 0.167 mmol) and methyl acrylate (0.5 mL, 5.5 mmol) were combined in a sealed tube and heated neat at 100° C. for 1 day, during which LC-MS indicated completion of reaction. The cooled reaction mixture was diluted with CH2Cl2 and washed with aqueous saturated NaHCO3 solution and brine. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. ISCO purification with 5% to 20% EtOAc/Hexanes afforded methyl 3-(1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)cyclopropylamino)propanoate as a light golden yellow oil. MS (ESI) m/z: Calculated: 487.6; Observed: 488.1 (M++1).

Workup

  1. customcompletion of reaction
  2. customThe cooled reaction mixture
  3. washwashed with aqueous saturated NaHCO3 solution and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customISCO purification with 5% to 20% EtOAc/Hexanes

Sources & evidence

ORD record
ord-731dada5d66d4ec196efe819078a9561
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

Loading…