Hydrochloric Acid → HCID 178474080, compound

HRID 1615337Notes

Reaction equation

HRID 1615337 reaction equation
[O:1]=[C:2]1[NH:3][C:4]2[C:9](/[C:10]/1=[CH:11]\[C:12]1[CH:20]=[C:19]3[C:15]([C:16](/[CH:29]=[CH:30]/[C:31]4[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=4)=[N:17][N:18]3COCC[Si](C)(C)C)=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[NH:37][C:38](=[O:40])[CH3:39].B(F)(F)F.CCOCC.Cl>>[O:1]=[C:2]1[NH:3][C:4]2[C:9](/[C:10]/1=[CH:11]\[C:12]1[CH:20]=[C:19]3[C:15]([C:16](/[CH:29]=[CH:30]/[C:31]4[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=4)=[N:17][NH:18]3)=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[NH:37][C:38](=[O:40])[CH3:39]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 68754755HCID 68754755, compound

Product 1

HCID 178474080HCID 178474080, compoundYield 71.2%

Procedure

According to the method of A57C, N-((E)-2-oxo-3-((3-((E)-2-(pyridin-4-yl)vinyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-6-yl)methylene)indolin-7-yl)acetamide (64 mg, 0.11 mmol) was treated with boron trifluoride etherate, followed by 2 N HCl to give the title compound as an orange solid (33 mg, 71%). 1H NMR (400 MHz, d6-DMSO) δ 10.33 (s, 1H), 9.42 (s, 1H), 8.85 (d, J=6.2 Hz, 2H), 8.46-8.30 (m, 4H), 7.98 (s, 1H), 7.87-7.78 (m, 2H), 7.80 (s, 1H), 7.63 (d, J=8.2 Hz, 1H), 7.42-7.35 (m, 2H), 6.81 (t, J=8.1 Hz, 1H), 2.05 (s, 3H); MS ESI 422.1 [M+H]+, calcd for [C25H19N5O2+H]+ 422.2.

Sources & evidence

ORD record
ord-83d38b468c4440588b9c8e0939511e02
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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