Triethylamine → HCID 67954844, compound

HRID 2383674Notes

Reaction equation

HRID 2383674 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]2=[CH:13][C:14]1[CH:22]=[C:21]2[C:17]([C:18](/[CH:23]=[CH:24]/[C:25]3[CH:26]=[N:27][C:28]([N:31]4[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]4)=[CH:29][CH:30]=3)=[N:19][NH:20]2)=[CH:16][CH:15]=1.[CH3:38]CN(CC)CC.CCOCC.C(Cl)Cl>C(Cl)(Cl)Cl.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C@:6]12[CH2:38][C@@H:13]1[C:14]1[CH:22]=[C:21]2[C:17]([C:18](/[CH:23]=[CH:24]/[C:25]3[CH:26]=[N:27][C:28]([N:31]4[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]4)=[CH:29][CH:30]=3)=[N:19][NH:20]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21881112Ethyl ether methylene chlorideHCID 178487097HCID 178487097, compound

Product 1

HCID 67954844HCID 67954844, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

From two repeated batches of Example A31 using 5-methoxy-3-((3-((E)-2-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)vinyl)-1H-indazol-6-yl)methylene)indolin-2-one (combined 491 mg, 1.0 mmol), purification using flash chromatography (silica gel, 1% Et3N in CHCl3/MeOH 96:4 to 92:8), followed by trituration with 1:1 Et2O/CH2Cl2 gave the minor diastereomer title compound as a pale yellow solid (18 mg, 4%). 1H NMR (400 MHz, CDCl3 with a few drops of CD3OD) δ ppm 8.21 (s, 1H), 7.82 (d, J=8.5 Hz, 1H), 7.75 (d, J=8.5 Hz, 1H), 7.39 (s, 1H), 7.27 (d, J=17.3 Hz, 1H), 7.16 (d, J=17.3 Hz, 1H), 7.05 (d, J=8.8 Hz, 1H), 6.80 (d, J=8.3 Hz, 1H), 6.72 (d, J=8.8 Hz, 1H), 6.67 (d, J=9.3 Hz, 1H), 6.54 (s, 1H), 3.77 (s, 3H), 3.58 (bs, 4H), 3.18-3.27 (m, 1H), 2.57 (bs, 4H), 2.40 (dd, J=8.5, 5.3 Hz, 1H), 2.35 (bs, 3H), 2.09 (dd, J=9.0, 5.0 Hz, 1H); MS ESI 507.3 [M+H]+, calcd for [C30H30N6O2+H]+ 507.2.

Sources & evidence

ORD record
ord-4c357161023a4ffc9c55409833d358bb
Source dataset
uspto-grants-2012_09
Patent number
US08263596B2

Reaction notes

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