Diisopropylethylamine → (5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-amine

HRID 605937

Reaction equation

CN1CCN(C2C=CC(NC3C4N(N=CN=4)C(C4C=C(C(N)=O)SC=4)=CN=3)=CC=2)CC1.[Br:32][C:33]1[N:38]2[N:39]=[CH:40][N:41]=[C:37]2[C:36](Br)=[N:35][CH:34]=1.[N:43]1([CH2:49][CH2:50][O:51][C:52]2[CH:57]=[CH:56][C:55]([NH2:58])=[CH:54][CH:53]=2)[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1.C(N(CC)C(C)C)(C)C>CC(O)C>[Br:32][C:33]1[N:38]2[N:39]=[CH:40][N:41]=[C:37]2[C:36]([NH:58][C:55]2[CH:56]=[CH:57][C:52]([O:51][CH2:50][CH2:49][N:43]3[CH2:44][CH2:45][O:46][CH2:47][CH2:48]3)=[CH:53][CH:54]=2)=[N:35][CH:34]=1

Participants

Conditions

Temperature: 95 °C

Procedure

According to the procedure described for Compound 6, step 1, 5,8-dibromo-[1,2,4]triazolo[1,5-a]pyrazine (0.5 g, 1.799 mmol), 4-(2-morpholin-4-yl-ethoxy)-phenylamine (0.6 g, 4.5 mmol) and N,N-diisopropylethylamine (0.47 mL, 2.7 mmol) in 2-propanol (6 mL) are stirred at 95° C. overnight. After evaporation of the solvent the residue is dissolved in DCM and washed with water (2×) and brine. The organic layer is dried over MgSO4, filtered and concentrated in vacuo to afford an oil purified by silica gel column chromatography. Elution with a 97:3 mixture DCM:MeOH gives the title compound (650 mg 86%) as a light yellow solid. LCMS: Rt 2.06 nm in (97.7%).

Workup

customAfter evaporation of the solvent the residue
dissolutionis dissolved in DCM
washwashed with water (2×) and brine
dry with materialThe organic layer is dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customto afford an oil
custompurified by silica gel column chromatography
washElution with a 97:3 mixture DCM

Sources & evidence

ORD record: ord-6cd305aa6b7140dfb87b95a3e98f61f4
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915256B2

Linked notes

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