Triethylamine → HCID 68997910, compound

HRID 1821391Notes

Reaction equation

HRID 1821391 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][O:21][CH2:20][CH2:19]3)[CH:15]=[CH:14][C:13]=2[NH2:24])=[N:2]1.C(N(CC)CC)C.[CH3:32][C:33]1[CH:37]=[CH:36][S:35][C:34]=1[C:38]([Cl:40])=[O:39].C(=O)([O-])O.[Na+]>C1COCC1>[ClH:40].[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][O:21][CH2:22][CH2:23]3)[CH:15]=[CH:14][C:13]=2[NH:24][C:38]([C:34]2[S:35][CH:36]=[CH:37][C:33]=2[CH3:32])=[O:39])=[N:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 27376053-Methyl-2-thenoyl ChlorideHCID 690043002-[2-(1H-indazol-3-yl)vinyl]-4-(morpholin-4-yl)phenylamine

Product 1

HCID 68997910HCID 68997910, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Example 1, (1H-indazol-3-ylmethyl)triphenylphosphonium bromide (0.12 g, 0.25 mmol) was dissolved in methanol (6.0 mL) and crude 3-{2-[5-(morpholin-4-yl)-2-nitrophenyl]vinyl}-1H-indazole was obtained from 5-morpholino-2-nitrobenzaldehyde (65 mg, 0.25 mmol) and potassium carbonate (0.10 g, 0.75 mmol). In a similar manner to Example 2, crude 3-{2-[5-(morpholin-4-yl)-2-nitrophenyl]vinyl}-1H-indazole (0.80 g, 2.3 mmol) was dissolved in ethanol (25 mL) and the solution was added with tin (0.82 g, 6.9 mmol) and concentrated hydrochloric acid (4.0 mL) and heated from room temperature to 40° C. to obtain 2-[2-(1H-indazol-3-yl)vinyl]-4-(morpholin-4-yl)phenylamine. Further, in a similar manner to Example 29, 2-[2-(1H-indazol-3-yl)vinyl]-4-(morpholin-4-yl)phenylamine (0.45 g, 1.4 mmol) was dissolved in THF (10 mL) and the solution was added with triethylamine (0.61 ml, 4.2 mmol) and 3-methylthiophenecarbonylchloride (0.20 g, 1.4 mmol) and stirred 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 free base of Compound 225. Further, said free base was treated by 4 mol/L hydrogen chloride-methanol solution (1.0 mL) to obtain Compound 225 (0.40 g, 55%).

Workup

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

Sources & evidence

ORD record
ord-08947b3d06c14ac38cc0af95ecfeb2f7
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

Loading…