2-Methoxyethanol → 4-[1,4,7]Triazonan-1-yl-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-2-ylamine

HRID 1027895Notes

Reaction equation

Cl[C:2]1[C:3]2[CH2:13][CH2:12][CH2:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1.Cl.Cl.Cl.[NH:21]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.CCN(C(C)C)C(C)C.COCCO>CCOCC>[N:21]1([C:2]2[C:3]3[CH2:13][CH2:12][CH2:11][C:10]4[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=4[C:4]=3[N:5]=[C:6]([NH2:8])[N:7]=2)[CH2:29][CH2:28][NH:27][CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1

Participants

Conditions

Temperature: 110 °C

Procedure

The product from Example 68A (52 mg, 0.212 mmol) was treated with 1,4,7-triazonane trihydrochloride (202 mg, 0.847 mmol), treated with Hunig's base (554 μl, 3.17 mmol), treated with 2-methoxyethanol (2116 μl), stirred at 110° C. for 19 hours, cooled, diluted with Et2O (25 mL), washed with 0.1 M NaOH (2×10 mL), washed with brine, dried (MgSO4), filtered, concentrated and purified by chromatography on silica gel (eluting with 2, 10 and 50% (9:1 MeOH:concentrated NH4OH) in CH2Cl2) to provide the title compound. 1H NMR (CD3OD) δ 2.08-2.24 (m, 2H), 2.40 (t, J=6.94 Hz, 2H), 2.67 (t, J=6.74 Hz, 2H), 2.94 (s, 4H), 3.10-3.16 (m, 4H), 3.71-3.77 (m, 4H), 7.24-7.29 (m, 1H), 7.32-7.41 (m, 2H), 7.63-7.68 (m, 1H); MS (M+H)+ m/z 339.

Workup

temperaturecooled
washwashed with 0.1 M NaOH (2×10 mL)
washwashed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
custompurified by chromatography on silica gel (eluting with 2, 10 and 50% (9:1 MeOH:concentrated NH4OH) in CH2Cl2)

Sources & evidence

ORD record: ord-5b5b8a1c35344719b89d332781639602
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735411B2

Reaction notes

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