Hydrochloric Acid → HCID 178478921, compound

HRID 1615321Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1/[CH:7]=[CH:8]/[C:9]1[C:17]2[C:12](=[CH:13][C:14](/[CH:18]=[C:19]3/[C:20](=[O:28])[NH:21][C:22]4[C:27]/3=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:15][CH:16]=2)[N:11](COCC[Si](C)(C)C)[N:10]=1.[ClH:37]>CCO.CC#N.CCOCC>[ClH:37].[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1/[CH:7]=[CH:8]/[C:9]1[C:17]2[C:12](=[CH:13][C:14]([CH:18]=[C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:21][C:20]3=[O:28])=[CH:15][CH:16]=2)[NH:11][N:10]=1

Participants

Conditions

Temperature: 77.5 °C

Procedure

A sealed, degassed mixture of (E)-3-((3-((E)-2-(1-methyl-1H-imidazol-2-yl)vinyl)1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-6-yl)methylene)indolin-2-one (35.4 mg, 0.071 mmol) in EtOH (4 mL) and aq HCl (4 M, 1 mL) was heated at 75-80° C. under Ar for 1 d. The reaction mixture was cooled to rt, diluted with MeCN (10 mL) and Et2O (5 mL) and stored at −20° C. overnight. The precipitate was collected by filtration, washed with MeCN to provide the title compound as a 1.5:1.0 (E:Z) mixture of isomers: a yellow solid (14.5 mg, 51%). 1H NMR (400 MHz, CD3OD) δ ppm 8.93 (s, 0.44H), 8.25 (d, J=8.28 Hz, 1.00H), 8.13 (d, J=8.53 Hz, 0.65H), 8.02-8.06 (m, 0.45H), 8.02 (s, 1.78H), 7.92-8.00 (m, 1.78H), 7.86-7.91 (m, 1.47H), 7.58-7.71 (m, 5.0H), 7.53 (d, J=16.81 Hz, 1.29H), 7.25 (t, J=7.65 Hz, 1.52H), 7.05 (t, J=7.78 Hz, 0.66H), 6.94 (d, J=7.78 Hz, 1.01H), 6.83-6.91 (m, 1.73H), 4.04 (s, 2.46H), 4.03 (s, 1.41H); MS ESI 368.1 [M+H]+, calcd for [C22H17N5O+H]+ 368.4.

Workup

customA sealed, degassed
temperatureThe reaction mixture was cooled to rt
filtrationThe precipitate was collected by filtration
washwashed with MeCN

Sources & evidence

ORD record: ord-a2934ba643b248a79e550fc14f027df5
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765748B2

Reaction notes

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