Ethylamine → HCID 49806032, compound

HRID 241207Notes

Reaction equation

CS[C:3]1[NH:7][C:6]2[CH:8]=[C:9]([C:12]3[CH:13]=[CH:14][C:15]4[O:21][CH2:20][CH2:19][N:18]([C:22]5[C:31]6[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=6)[N:25]=[CH:24][CH:23]=5)[CH2:17][C:16]=4[CH:32]=3)[CH:10]=[CH:11][C:5]=2[N:4]=1.[CH2:33]([NH2:35])[CH3:34]>C(O)C>[CH2:33]([NH:35][C:3]1[NH:7][C:6]2[CH:8]=[C:9]([C:12]3[CH:13]=[CH:14][C:15]4[O:21][CH2:20][CH2:19][N:18]([C:22]5[C:31]6[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=6)[N:25]=[CH:24][CH:23]=5)[CH2:17][C:16]=4[CH:32]=3)[CH:10]=[CH:11][C:5]=2[N:4]=1)[CH3:34]

Participants

Conditions

Temperature: 150 °C

Procedure

A solution of 7-[2-(methylthio)-1H-benzimidazol-6-yl]-4-quinolin-4-yl-2,3,4,5-tetra-hydro-1,4-benzoxazepine (52 mg, 0.12 mmol, prepared according to the method of example 19) and ethylamine (1.5 mL) in ethanol (3 mL) heated with microwave irradiation at 150° C. for 8 h. Purification of the crude material by preparative reverse phase HPLC (0.1% aqueous ammonium acetate-acetonitrile) provided the title Compound as acetate salt (4 mg, 7% yield) as a colorless solid. 1H NMR (400 MHz, methanol-d4): 8.55 (d, 1H), 8.15 (d, 1H), 7.95 (d, 1H), 7.73 (m, 1H), 7.60-7.50 (m, 3H), 7.42 (m, 1H), 7.33 (dd, 1H), 7.29 (d, 1H), 7.09 (m, 2H), 4.69 (s, 2H), 4.41 (m, 2H), 3.92 (m, 2H), 3.44 (q, 2H), 1.94 (s, 3H), 1.31 (t, 3H); MS (EI) for C27H25N5O: 436 (MH+).

Workup

customPurification of the crude material by preparative reverse phase HPLC (0.1% aqueous ammonium acetate-acetonitrile)

Sources & evidence

ORD record: ord-3cf7c528367f4f39b6c934e24d2eb8f7
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648066B2

Reaction notes

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