Triethylamine → methyl 2-(6-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)-3,4-dihydroisoquinolin-2(1H)-yl)acetate

HRID 1177588Notes

Reaction equation

[C:1]1([C:7]2([C:10]3[N:15]=[C:14]4[S:16][C:17]([C:19]5[CH:20]=[C:21]6[C:26](=[CH:27][CH:28]=5)[CH2:25][NH:24][CH2:23][CH2:22]6)=[N:18][C:13]4=[CH:12][CH:11]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Br[CH2:37][C:38]([O:40][CH3:41])=[O:39]>C(Cl)Cl>[C:1]1([C:7]2([C:10]3[N:15]=[C:14]4[S:16][C:17]([C:19]5[CH:20]=[C:21]6[C:26](=[CH:27][CH:28]=5)[CH2:25][N:24]([CH2:37][C:38]([O:40][CH3:41])=[O:39])[CH2:23][CH2:22]6)=[N:18][C:13]4=[CH:12][CH:11]=3)[CH2:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 5-(1-phenylcyclopropyl)-2-(1,2,3,4-tetrahydroisoquinolin-6-yl)thiazolo[5,4-b]pyridine (97 mg, 0.252 mmol), triethylamine (0.053 mL, 0.377 mmol), and methyl 2-bromoacetate (0.024 mL, 0.254 mmol) in DCM (2.0 mL) was stirred at 25° C. for 30 min. Additional methyl 2-bromoacetate (0.024 mL, 0.254 mmol) was then added, and the resulting mixture was stirred at 25° C. for 30 min. The resulting suspension was then concentrated onto silica gel and chromatographically purified (0-100% EtOAc/hexanes) to provide methyl 2-(6-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)-3,4-dihydroisoquinolin-2(1H)-yl)acetate as a white solid. MS (ESI) m/z: Calculated: 455.2; Observed: 456.0 (M++1).

Workup

stirringthe resulting mixture was stirred at 25° C. for 30 min
concentrationThe resulting suspension was then concentrated onto silica gel
customchromatographically purified (0-100% EtOAc/hexanes)

Sources & evidence

ORD record: ord-6a0278365e094f23bc125a4a6b0f6f68
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

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