Dichloromethane → Methyl 3-(5-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)isoindolin-2-yl)propanoate

HRID 1177653Notes

Reaction equation

HRID 1177653 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[S:11][C:12]4[C:17]([N:18]=3)=[CH:16][CH:15]=[C:14]([C:19]3([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[CH2:21][CH2:20]3)[N:13]=4)=[CH:7][CH:8]=2)[CH2:3][NH:2]1.C(Cl)Cl.[C:31]([O:35][CH2:36]C)(=[O:34])[CH:32]=[CH2:33].CN1CCCN2CCCN=C12>CO>[C:22]1([C:19]2([C:14]3[N:13]=[C:12]4[S:11][C:10]([C:6]5[CH:5]=[C:4]6[C:9](=[CH:8][CH:7]=5)[CH2:1][N:2]([CH2:33][CH2:32][C:31]([O:35][CH3:36])=[O:34])[CH2:3]6)=[N:18][C:17]4=[CH:16][CH:15]=3)[CH2:20][CH2:21]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8821Ethyl AcrylateHCID 1235837-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-eneHCID 671117342-(Isoindolin-5-yl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine

Product 1

HCID 67111825Methyl 3-(5-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)isoindolin-2-yl)propanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(Isoindolin-5-yl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine (75 mg, 0.203 mmol) was dissolved in methanol (2.0 mL) and DCM (1 mL) before ethyl acrylate (27.1 μL, 0.244 mmol) and 1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine (1.457 μL, 10.15 μmol) were added and stirred at ambient temperature for 16 h. Methyl 3-(5-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)isoindolin-2-yl)propanoate was obtained after purification via flash chromatography. MS (ESI) m/z: Calculated: 455.2; Observed: 456.4 (M++H).

Sources & evidence

ORD record
ord-587233ea3c6a47a8b510724abd382d03
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

Loading…