Triethylamine → HCID 44250434, compound

HRID 2189483Notes

Reaction equation

HRID 2189483 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:13])=O)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[Cl:14][C:15]1[C:20]([O:21][C:22]2[N:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=2)=[CH:19][CH:18]=[CH:17][N:16]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[Cl:14][C:15]1[C:20]([O:21][C:22]2[N:27]=[CH:26][C:25]([NH:28][C:11]([C:6]3[C:5]4[C:9](=[CH:10][C:2]([CH3:1])=[CH:3][CH:4]=4)[NH:8][CH:7]=3)=[O:13])=[CH:24][CH:23]=2)=[CH:19][CH:18]=[CH:17][N:16]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 183852116-Methyl-1H-indole-3-carboxylic acidHCID 876387346-[(2-Chloro-3-pyridinyl)oxy]-3-pyridinamine

Product 1

HCID 44250434HCID 44250434, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

The 6-methyl-1H-indole-3-carboxylic acid (50 mg, 0.28 mmol) in Example 16 and the 6-(2-chloropyridine-3-yloxy)-pyridine-3-amine (60 mg, 0.28 mmol) in Example 22 were dissolved in DMF (5 ml), HBTU (100 mg, 0.28 mmol) and triethylamine (0.11 ml, 0.84 mmol) were added to the solution, and the mixture was stirred at 80° C. for 8 hours. After the reaction was completed, the product was washed and filtered to yield a target compound as a white solid (18 ml, 34%) by chromatography (methanol:dichloroinethane=1:30).

Workup

  1. washthe product was washed
  2. filtrationfiltered

Sources & evidence

ORD record
ord-14951823e35741b0847ff7507ce37e6e
Source dataset
uspto-grants-2012_12
Patent number
US08324246B2

Reaction notes

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