HCID 86647860, compound → ethyl {6-[4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]-1H-imidazo[4,5-b]pyridin-2-yl}carbamate

HRID 241229Notes

Reaction equation

[NH2:1][C:2]1[C:3]([NH:31][C:32]([NH:34][C:35](=[O:39])[O:36][CH2:37][CH3:38])=C)=[N:4][CH:5]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]3[O:17][CH2:16][CH2:15][N:14]([C:18]4[C:27]5[CH2:26][C:25]([CH3:29])([CH3:28])[CH2:24][CH2:23][C:22]=5[N:21]=[CH:20][N:19]=4)[CH2:13][C:12]=3[CH:30]=2)[CH:7]=1>O1CCCC1.[Hg]=O>[CH3:28][C:25]1([CH3:29])[CH2:24][CH2:23][C:22]2[N:21]=[CH:20][N:19]=[C:18]([N:14]3[CH2:13][C:12]4[CH:30]=[C:8]([C:6]5[CH:7]=[C:2]6[NH:1][C:32]([NH:34][C:35](=[O:39])[O:36][CH2:37][CH3:38])=[N:31][C:3]6=[N:4][CH:5]=5)[CH:9]=[CH:10][C:11]=4[O:17][CH2:16][CH2:15]3)[C:27]=2[CH2:26]1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of ethyl [1-({3-amino-5-[4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]pyridine-2-yl}amino)ethenyl]carbamate (82 mg, 0.15 mmol) and mercury(II) oxide (33 mg, 0.15 mmol) in tetrahydrofuran (8 mL) was stirred at 70° C. for 24 h. On cooling to room temperature, the mixture filtered then concentrated and the residue purified by preparative reverse phase HPLC to afford the title Compound (6 mg, 3% yield over 2 steps) as a colorless solid. 1H NMR (400 MHz, methanol-d4): 8.51 (s, 1H), 8.49 (d, 1H), 8.22 (d, 1H), 7.72 (d, 1H), 7.66 (dd, 1H), 7.09 (d, 1H), 5.17 (s, 2H), 4.48 (m, 2H), 4.36 (q, 2H), 4.33 (m, 2H), 2.85 (m, 2H), 2.60 (s, 2H), 1.69 (m, 2H), 1.38 (t, 3H), 0.95 (s, 6H); MS (EI) for C28H31N7O3: 514 (MH+).

Workup

temperatureOn cooling to room temperature
filtrationthe mixture filtered
concentrationthen concentrated
customthe residue purified by preparative reverse phase HPLC

Sources & evidence

ORD record: ord-d1b33832d18f41e8b6047c2035cfb823
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648066B2

Reaction notes

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