Methyl Acrylate → HCID 67111470, compound

HRID 1177467Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:26]([NH2:29])([CH3:28])[CH3:27])[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]([NH:29][CH2:32][CH2:31][C:30]([O:34][CH3:35])=[O:33])([CH3:27])[CH3:28])[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:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:18][CH2:19]1)[N:11]=2

Participants

Conditions

Temperature: 100 °C

Procedure

2-(3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)-propan-2-amine (0.081 g, 0.20 mmol) and methyl acrylate (0.18 mL, 2.00 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 25% EtOAc/Hexanes afforded methyl 3-(2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)propan-2-ylamino)propanoate as a white amorphous solid. MS (ESI) m/z: Calculated: 489.2; Observed: 490.1 (M++1).

Workup

customcompletion of reaction
customThe cooled reaction mixture
washwashed with aqueous saturated NaHCO3 solution and brine
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customISCO purification with 5% to 25% EtOAc/Hexanes

Sources & evidence

ORD record: ord-4b987962e15f41829e9c34e53d0bb515
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

Loading…