HCID 67050780, compound → HCID 58204946, compound

HRID 886468Notes

Reaction equation

COC1C=C(C=CC=1OC)C[NH:7][C:8]1[N:30]=[CH:29][C:11]2[C:12]3[N:13]([CH:17]=[C:18]([C:20]4[N:24]([CH:25]([CH3:27])[CH3:26])[N:23]=[C:22]([CH3:28])[N:21]=4)[N:19]=3)[CH2:14][CH2:15][O:16][C:10]=2[CH:9]=1>C(O)(C(F)(F)F)=O>[CH:25]([N:24]1[C:20]([C:18]2[N:19]=[C:12]3[C:11]4[CH:29]=[N:30][C:8]([NH2:7])=[CH:9][C:10]=4[O:16][CH2:15][CH2:14][N:13]3[CH:17]=2)=[N:21][C:22]([CH3:28])=[N:23]1)([CH3:27])[CH3:26]

Participants

Conditions

Temperature: 65 °C

Procedure

N-(3,4-dimethoxybenzyl)-2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-amine (190 mg, 0.40 mmol) was dissolved in TFA (3.0 mL) and heated at 65° C. for 30 min. The reaction mixture was cooled to ambient temperature and concentrated to dryness in vacuo. The crude residue was purified via HPLC to afford 463 as a white solid (40 mg, 31%). LC/MS (ESI+): m/z 326 (M+H). 1H NMR (400 MHz, DMSO) δ 8.92 (s, 1H), 7.76 (s, 1H), 6.19 (s, 2H), 5.98 (s, 1H), 5.88-5.76 (m, 1H), 4.45 (dd, J=14.4, 5.6 Hz, 4H), 2.24 (s, 3H), 1.44 (d, J=6.6 Hz, 6H)

Workup

temperatureThe reaction mixture was cooled to ambient temperature
concentrationconcentrated to dryness in vacuo
customThe crude residue was purified via HPLC

Sources & evidence

ORD record: ord-1196d1803c154b6591ab5d11108d4804
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242104B2

Reaction notes

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