Ammonia → HCID 68579549, compound

HRID 2233985Notes

Reaction equation

HRID 2233985 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[N:23]=[C:22]([S:24][CH:25]([CH3:27])[CH3:26])[N:21]=[C:20]([C:28]([OH:30])=O)[CH:19]=2)[CH2:14][CH2:13]1)=[O:10].N.C[N:33](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O.O>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[N:23]=[C:22]([S:24][CH:25]([CH3:27])[CH3:26])[N:21]=[C:20]([C:28]([NH2:33])=[O:30])[CH:19]=2)[CH2:14][CH2:13]1)=[O:10]

Participants

7

Reactant 3

HCID 222AmmoniaHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68579969HCID 68579969, compound

Product 1

HCID 68579549HCID 68579549, compoundYield 157.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-2-(isopropylthio)pyrimidine-4-carboxylic acid (Example 180; 200 mg, 0.423 mmol), ammonia solution (2 M in MeOH, 0.43 ml, 0.846 mmol), TEA (0.06 ml, 0.423 mmol), and HATU (161 mg, 0.42 mmol) were combined in DMF (3 ml) and stirred at room temperature for 1 h. The reaction was diluted with EtOAc and water, and the organic portion was washed sequentially with 1 N HCl, saturated sodium bicarbonate, and brine. The organic portion was dried over sodium sulfate, filtered and concentrated to give an off-white solid (312 mg). The crude material was purified by preparatory HPLC using a gradient of 40-70% acetonitrile/water (0.1% TFA) over 14 minutes to give the title compound as a white solid.

Workup

  1. washthe organic portion was washed sequentially with 1 N HCl, saturated sodium bicarbonate, and brine
  2. dry with materialThe organic portion was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bc44e17cc5eb4738917b4f67c44cc644
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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