Triethylamine → HCID 68996678, compound

HRID 1821393Notes

Reaction equation

HRID 1821393 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[CH:11][C:12]2[CH:17]=[C:16]([N:18]3[CH2:23][CH2:22][CH:21]([S:24]([CH3:27])(=[O:26])=[O:25])[CH2:20][CH2:19]3)[CH:15]=[CH:14][C:13]=2[NH2:28])=[N:2]1.C(N(CC)CC)C.[CH3:36][C:37]1[CH:41]=[CH:40][S:39][C:38]=1[C:42](Cl)=[O:43].C(=O)([O-])O.[Na+]>C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[C:16]([N:18]3[CH2:19][CH2:20][CH:21]([S:24]([CH3:27])(=[O:25])=[O:26])[CH2:22][CH2:23]3)[CH:15]=[CH:14][C:13]=2[NH:28][C:42]([C:38]2[S:39][CH:40]=[CH:41][C:37]=2[CH3:36])=[O:43])=[N:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 27376053-Methyl-2-thenoyl ChlorideHCID 69000917HCID 69000917, compound

Product 1

HCID 68996678HCID 68996678, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Example 2, said crude 3-{2-[5-(4-methanesulfonylpiperidin-1-yl)-2-nitrophenyl]vinyl}-1H-indazole (0.23 g, 0.54 mmol) obtained in Step 1 was dissolved in ethanol (7.0 mL) and 2-[2-(1H-indazol-3-yl)vinyl]-4-(4-methanesulfonylpiperidin-1-yl)phenylamine was obtained from tin (0.19 g, 1.6 mmol) and concentrated hydrochloric acid (1.0 mL) at room temperature. In a similar manner to Example 29, a solution of 2-[2-(1H-indazol-3-yl)vinyl]-4-(4-methanesulfonylpiperidin-1-yl)phenylamine (0.22 g, 0.54 mmol) in THF (10 mL) was added with triethylamine (0.23 ml, 1.6 mmol) and 3-methylthiophenecarbonyl chloride (0.09 g, 0.54 mmol), followed by stirring at room temperature for 1 hour. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution, extracted with ethyl acetate and the organic layer was concentrated under reduced pressure to obtain crude (E)-N-{2-[2-(1H-indazol-3-yl)vinyl]-4-(4-methanesulfonylpiperidin-1-yl)phenyl}-3-methylthiophene-2-carboxamide. Further, Compound 227 (68 mg, 22%) was obtained using 4 mol/L hydrogen chloride-methanol solution (1.0 mL).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationthe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bc272fabc767454faa5a44171639fa5e
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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