Acetic Anhydride → N-(4,5,6,7-tetrahydro-5-(5,6-dimethoxypyrazin-2-yl)thiazolo[5,4-c]pyridin-2-yl)acetamide

HRID 39360Notes

Reaction equation

HRID 39360 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]([N:11]2[CH2:16][CH2:15][C:14]3[N:17]=[C:18]([NH2:20])[S:19][C:13]=3[CH2:12]2)=[N:7][C:8]=1[O:9][CH3:10].CCN(C(C)C)C(C)C.[C:30](OC(=O)C)(=[O:32])[CH3:31]>C(Cl)Cl>[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]([N:11]2[CH2:16][CH2:15][C:14]3[N:17]=[C:18]([NH:20][C:30](=[O:32])[CH3:31])[S:19][C:13]=3[CH2:12]2)=[N:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 866619525-(5,6-Dimethoxypyrazin-2-yl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-amine

Product 1

HCID 46872069N-(4,5,6,7-tetrahydro-5-(5,6-dimethoxypyrazin-2-yl)thiazolo[5,4-c]pyridin-2-yl)acetamideYield 49.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As shown in step 9-vi of Scheme 9, to a solution of Compound 1032 (65.4 mg, 0.223 mmol) in DCM (2 mL) was added DIEA (200 μL, 1.148 mmol) and acetic anhydride (200 μL, 2.12 mmol). The reaction solution was stirred at room temperature for 150 min and the crude produce purified by medium pressure silica gel chromatography (10 to 80% EtOAc in Hexanes) to give N-(4,5,6,7-tetrahydro-5-(5,6-dimethoxypyrazin-2-yl)thiazolo[5,4-c]pyridin-2-yl)acetamide (Compound 14, 36.8 mg) as an off white solid, which was salted as its mono-mesylate salt to yield a beige solid: ESMS (M+H) 336.12; 1H NMR (300.0 MHz, DMSO-d6) δ 7.31 (s, 1H), 4.55 (s, 2H), 3.91 (m, 3H), 3.83 (m, 5H), 2.73 (t, J=5.4 Hz, 2H), 2.39 (d, J=0.6 Hz, 3H) and 2.12 (s, 3H) ppm.

Workup

  1. customthe crude produce
  2. custompurified by medium pressure silica gel chromatography (10 to 80% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-0912db0cd489499ea55d404d14a6cb45
Source dataset
uspto-grants-2013_09
Patent number
US08524906B2

Reaction notes

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