Triethylamine → HCID 69002932, compound

HRID 1821400Notes

Reaction equation

HRID 1821400 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([OH:9])=O.S(Cl)([Cl:12])=O.[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16](/[CH:23]=[CH:24]/[C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[CH:27][C:26]=2[NH2:37])=[N:15]1.C(N(CC)CC)C.Cl.C(O)C>CN(C=O)C>[ClH:12].[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16](/[CH:23]=[CH:24]/[C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH2:32][CH2:33][O:34][CH2:35][CH2:36]3)=[CH:27][C:26]=2[NH:37][C:7]([C:3]2[S:4][CH:5]=[CH:6][C:2]=2[CH3:1])=[O:9])=[N:15]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 902693-Methyl-2-thenoic acidHCID 21887872Ethanol hydrochlorideHCID 69000941HCID 69000941, compound

Product 1

HCID 69002932HCID 69002932, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar manner to Example 29, a free base of Compound 247 was synthesized from 3-methylthiophene-2-carboxylic acid (0.13 g, 0.94 mmol), thionyl chloride (0.10 mL, 1.4 mmol), DMF (few drops), (E)-2-[2-(1H-indazol-3-yl)vinyl]-5-(morpholin-4-yl)phenylamine (0.10 g, 0.31 mmol) obtained in Step 2 of Example 246 and triethylamine (0.13 mL, 0.94 mmol). Further, said free base was added with 1 mol/L hydrogen chloride-ethanol solution (2.0 mL), stirred for 1 hour and then the reaction mixture was concentrated. The residue was triturated in acetone to obtain Compound 247 (61 mg, 44%).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customThe residue was triturated in acetone

Sources & evidence

ORD record
ord-2f5140f685c247d49512e0b33ff8c71f
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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