Acrylic Acid → 3-(6-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)-3,4-dihydroisoquinolin-2(1H)-yl)propanoic acid

HRID 1177587Notes

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:29]([OH:33])(=[O:32])[CH:30]=[CH2:31].CCN(C(C)C)C(C)C>CO>[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]([CH2:31][CH2:30][C:29]([OH:33])=[O:32])[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: 63 °C

Procedure

A mixture of 5-(1-phenylcyclopropyl)-2-(1,2,3,4-tetrahydroisoquinolin-6-yl)thiazolo[5,4-b]pyridine (28.1 mg, 0.073 mmol), acrylic acid (7.54 μl, 0.110 mmol), and DIPEA (1.276 μl, 7.33 μmol) in methanol (0.80 mL) was stirred at 63° C. for 1 d. The resulting suspension was then concentrated in vacuo, and the residue was taken up in DMSO (2.0 mL)+TFA (50 μL) and purified by rpHPLC (10-100% CH3CN/H2O+0.1% TFA) to provide 3-(6-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)-3,4-dihydroisoquinolin-2(1H)-yl)propanoic acid as a yellow solid. MS (ESI) m/z: Calculated: 455.2; Observed: 456.1 (M++1).

Workup

concentrationThe resulting suspension was then concentrated in vacuo
custompurified by rpHPLC (10-100% CH3CN/H2O+0.1% TFA)

Sources & evidence

ORD record: ord-164a61a2192a4c808a88936e824abc70
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

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