Diisopropylethylamine → HCID 90260024, compound

HRID 1478134Notes

Reaction equation

HRID 1478134 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[CH:12]=[C:11]([C:13]([OH:15])=O)[NH:10][C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2].[CH3:16][N:17](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.CN>CN(C=O)C>[CH3:16][NH:17][C:13]([C:11]1[NH:10][C:7]2=[N:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[C:6]2[CH:12]=1)=[O:15]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 401519725-Nitro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid

Product 1

HCID 90260024HCID 90260024, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-nitro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (1.3 g, 6.5 mmoles), HATU (1.2 eq) and DIEA (5 eq) were dissolved in dry DMF under argon. After stirring at RT for 15 minutes, methylamine hydrochloride (3 eq) was added and the mixture was allowed to stir at RT overnight. The mixture was concentrated and washed by a saturated solution of sodium carbonate. The precipitate was filtered off, washed with water and diethyl ether to obtain a brownish solid (1.1 g, 5 mmoles). Yield=77%. ESI-MS: m/z 221 ([M+H]+). HPLC purity: 98%.

Workup

  1. stirringto stir at RT overnight
  2. concentrationThe mixture was concentrated
  3. washwashed by a saturated solution of sodium carbonate
  4. filtrationThe precipitate was filtered off
  5. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-ff4251897eed41faa4b548199923eeca
Source dataset
uspto-grants-2016_08
Patent number
US09403823B2

Reaction notes

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