Hydrochloric Acid → HCID 178517068, compound

HRID 1615270Notes

Reaction equation

HRID 1615270 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[N:11]1[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]2[CH:27]=[C:26]([CH:28]=O)[CH:25]=[C:24]3[C:20]=2[CH:21]=[N:22][N:23]3COCC[Si](C)(C)C)=[CH:13][CH:12]=1.Cl>>[N:11]1[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]2[CH:27]=[C:26]([CH:28]=[C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][C:2]3=[O:10])[CH:25]=[C:24]3[C:20]=2[CH:21]=[N:22][NH:23]3)=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 321710OxindoleHCID 86651955HCID 86651955, compound

Product 1

HCID 178517068HCID 178517068, compound

Procedure

According to the method of A54C, oxindole (10 mg, 0.07 mmol) was reacted with (E)-4-(2-(pyridin-4-yl)vinyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carb-aldehyde (27 mg, 0.06 mmol) and then treated with HCl to give the title compound as a 3:1 mixture of E/Z isomers (4 mg, 28%). MS ESI [M+H]+, calcd for [C23H16N4O+H]+ 365.1; found m/z 365.2. E-isomer 1H NMR (400 MHz, DMSO-d6) δ 8.82-8.79 (m, 2H), 8.20-8.12 (m, 3H), 7.96 (s, 1H), 7.81-7.74 (m, 3H), 7.64 (s, 1H), 7.52 (d, 1H, J=8.1 Hz), 7.23 (t, 1H, J=7.8 Hz), 6.89 (d, 1H, J=8.0 Hz), 6.88-6.86 (m, 1H); Z-isomer 1H NMR (400 MHz, DMSO-d6) δ 8.97 (s, 1H), 8.67 (s, 1H), 8.60-8.58 (m, 2H), 8.27 (s, 1H), 8.01 (s, 1H), 7.91 (d, 1H, J=16.8 Hz), 7.77 (d, 1H, J=7.5 Hz), 7.74 (d, 2H, J=5.5 Hz), 7.49 (d, 1H, J=16 Hz), 7.23 (t, 1H, J=7.8 Hz), 7.02 (t, 1H, J=7.6 Hz), 6.86 (d, 1H, J=7.6 Hz).

Sources & evidence

ORD record
ord-91932928a8244e3a896d4751c9125458
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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