Hydrochloric Acid → HCID 178517049, compound

HRID 1615372Notes

Reaction equation

HRID 1615372 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:43]=[CH:42][C:11]([CH:12]=[CH:13][C:14]3[C:22]4[C:17](=[CH:18][C:19](/[CH:23]=[C:24]5/[C:25](=[O:33])[NH:26][C:27]6[C:32]/5=[CH:31][CH:30]=[CH:29][CH:28]=6)=[CH:20][CH:21]=4)[N:16](COCC[Si](C)(C)C)[N:15]=3)=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.B(F)(F)F.CCOCC.Cl>>[O:1]1[CH2:2][CH2:3][N:4]([CH2:7][C:8]2[CH:43]=[CH:42][C:11]([CH:12]=[CH:13][C:14]3[C:22]4[C:17](=[CH:18][C:19](/[CH:23]=[C:24]5/[C:25](=[O:33])[NH:26][C:27]6[C:32]/5=[CH:31][CH:30]=[CH:29][CH:28]=6)=[CH:20][CH:21]=4)[NH:16][N:15]=3)=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 68754821HCID 68754821, compound

Product 1

HCID 178517049HCID 178517049, compoundYield 44.6%

Procedure

According to the method of A57C, (E)-3-((3-(4-(morpholinomethyl)styryl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-6-yl)methylene)indolin-2-one (95 mg, 0.16 mmol) was treated with boron trifluoride etherate, followed by 2 N HCl to give the title compound as an orange solid (33 mg, 42%). 1H NMR (400 MHz, CD3OD) δ 8.21 (d, J=8.4 Hz, 1H), 7.85 (d, J=6.0 Hz), 7.78 (d, J=8.2 Hz, 2H), 7.66 (d, J=7.6 Hz, 1H), 7.53-7.58 (m, 5H), 7.24 (t, J=7.7 Hz, 1H), 6.93 (d, J=7.6 Hz, 1H), 6.87 (td, J=6.7 Hz, 0.9 Hz, 1H), 4.39 (s, 2H), 4.05-4.09 (m, 2H), 3.72-3.78 (m, 2H), 3.40-3.43 (m, 2H), 3.21-3.26 (m, 2H); MS ESI 463.3 [M+H]+, calcd for [C29H26N4O2+H]+ 463.2.

Sources & evidence

ORD record
ord-21399f8202f44a728f86cbcdd1e4030c
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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