Ammonium Chloride → HCID 68291788, compound

HRID 1408971Notes

Reaction equation

HRID 1408971 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([NH:10][C@@H:11]3[CH2:15][CH2:14][C@:13]([CH3:19])([C:16]([OH:18])=O)[C:12]3([CH3:21])[CH3:20])=[C:8]([C:22](=[O:24])[NH2:23])[CH:7]=[N:6][N:5]2[CH:25]=1.CC[N:28](C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([NH:10][C@@H:11]3[CH2:15][CH2:14][C@@:13]([C:16](=[O:18])[NH2:28])([CH3:19])[C:12]3([CH3:21])[CH3:20])=[C:8]([C:22]([NH2:23])=[O:24])[CH:7]=[N:6][N:5]2[CH:25]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68358955HCID 68358955, compound

Product 1

HCID 68291788HCID 68291788, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

To a stirred solution of (1S,3R)-3-(6-bromo-3-carbamoylpyrrolo[1,2-b]pyridazin-4-ylamino)-1,2,2-trimethylcyclopentanecarboxylic acid (182 mg, 0.445 mmol) in DMF (3.0 ml), were added Hunig's base (582 μl, 3.34 mmol) and HATU (254 mg, 0.667 mmol). After 15 minutes, ammonium chloride (119 mg, 2.223 mmol) was added. The reaction was heated at 75° C. for 24 hrs. The reaction mixture was cooled to room temperature and diluted with ethyl acetate. The solution was washed successively with water, (sat.) ammonium chloride and (sat.) sodium chloride. The ethyl acetate extract was dried with sodium sulfate, filtered, and concentrated under reduced pressure to yield the title compound (104 mg, 0.255 mmol, 57.3% yield) as a white solid. LC/MS found [M+H]+=409.9.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe solution was washed successively with water, (sat.) ammonium chloride and (sat.) sodium chloride
  3. extractionThe ethyl acetate extract
  4. dry with materialwas dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b4a213210fc4401d992daf3adccbe49d
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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