HCID 68732814, compound → HCID 178483851, compound

HRID 1615347Notes

Reaction equation

HRID 1615347 reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][N:5]([CH3:19])[S:6]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH2:12]2)(=[O:8])=[O:7].[N:21]1[CH:26]=[CH:25][C:24](/[CH:27]=[CH:28]/[C:29]2[C:37]3[C:32](=[CH:33][C:34]([CH:38]=O)=[CH:35][CH:36]=3)[N:31](COCC[Si](C)(C)C)[N:30]=2)=[CH:23][CH:22]=1>>[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][N:5]([CH3:19])[S:6]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[C:12]2=[CH:38][C:34]1[CH:33]=[C:32]2[C:37]([C:29](/[CH:28]=[CH:27]/[C:24]3[CH:23]=[CH:22][N:21]=[CH:26][CH:25]=3)=[N:30][NH:31]2)=[CH:36][CH:35]=1)(=[O:8])=[O:7]

Participants

3

Reactant 2

HCID 68732814HCID 68732814, compoundHCID 86651957HCID 86651957, compound

Product 1

HCID 178483851HCID 178483851, compound

Procedure

The title compound was synthesized according to the method described in Example A57 from N-(2-(dimethylamino)ethyl)-N-methyl-2-oxoindoline-5-sulfonamide and (E)-3-(2-(pyridin-4-yl)vinyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde (25 mg, 0.065 mmol) with a modified purification procedure. The product was extracted into EtOAc, and washed with NaHCO3(sat) (2×), brine (2×) and the organic layer dried over MgSO4. After removal of solvent the resulting yellow solid was titurated with Et2O/hexanes to give after drying 1.5 mg, 4.1% yield of a yellow solid which was a 77:23 mixture of (E)/(Z) isomers. 1H NMR (400 MHz, CD3OD) δ 9.01, 8.03 (s, 1H), 8.55-8.45 (m, 2H), 8.30-8.05 (m, 3H), 7.96-7.76 (m, 2H), 7.75-7.65 (m, 3H), 7.58-7.51 (m, 1H), 7.10, 7.07 (d, J=8.6 Hz, 1H), 3.05-2.99 (m, 2H), 2.90, 2.72 (m, 2H), 2.80, 2.63 (s, 3H), 2.57, 2.34 (s, 6H); MS ESI 529.2 [M+H]+, calcd for [C28H28N6O3S+H]+ 529.20.

Workup

  1. extractionThe product was extracted into EtOAc
  2. washwashed with NaHCO3(sat) (2×), brine (2×)
  3. dry with materialthe organic layer dried over MgSO4
  4. customAfter removal of solvent the resulting yellow solid
  5. customto give

Sources & evidence

ORD record
ord-af8849edcb3a48078453d76949e2da2e
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

Loading…