Hydrochloric Acid → HCID 178479642, compound

HRID 1615352Notes

Reaction equation

HRID 1615352 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/[C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH:18]=[C:19]4[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[NH:21][C:20]4=[O:28])[CH:16]=3)[N:11](COCC[Si](C)(C)C)[N:10]=2)=[CH:3][CH:2]=1.B(F)(F)F.CCOCC.[ClH:46]>>[ClH:46].[N:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/[C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH:18]=[C:19]4[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[NH:21][C:20]4=[O:28])[CH:16]=3)[NH:11][N:10]=2)=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 8000Boron trifluoride etherateHCID 698107823-((3-((E)-2-(pyridin-4-yl)vinyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-5-yl)methylene)indolin-2-one

Product 1

HCID 178479642HCID 178479642, compound

Procedure

According to the method of A57C and D, 3-((3-((E)-2-(pyridin-4-yl)vinyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-5-yl)methylene)indolin-2-one (13.1 mg, 0.026 mmol) was treated with boron trifluoride etherate, followed by 2 N HCl (water/EtOH) treatment. Suction filtration gave a solid which was rinsed with 1:1 EtOH:water (2×1 mL). Pumping under high vacuum gave an orange solid (7.3 mg, 69%, 55:45 mixture of E/Z isomers, HCl salt). 1H NMR (400 MHz, CD3OD) δ 9.83 (s, 0.4H), 8.73 (m, 2H), 8.59 (s, 0.6H), 8.33-8.20 (m, 3.5H), 7.95 (m, 1H), 7.91-7.87 (m, 1H), 7.80-7.63 (m, 3H), 7.25 (t, J=8.4 Hz, 1H), 7.07 (t, J=7.6 Hz, 0.4H), 6.96-6.87 (m, 1.6H); MS ESI 365.2 [M+H]+, calcd for [C23H16N4O+H]+ 365.14.

Workup

  1. filtrationSuction filtration
  2. customgave a solid which
  3. washwas rinsed with 1:1 EtOH
  4. customgave

Sources & evidence

ORD record
ord-cd99295c08784a978db25b43cfaa5c44
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

Loading…