Hydrochloric Acid → HCID 66593309, compound

HRID 1091668Notes

Reaction equation

HRID 1091668 reaction equation
[C:1]([C:4]1[CH:26]=[CH:25][C:7]2[NH:8][C:9](=[C:11]([C:15]3[N:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][N:16]=3)[C:12]([NH2:14])=[O:13])[NH:10][C:6]=2[CH:5]=1)([OH:3])=O.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:60]1([CH2:66][CH2:67][CH2:68][NH2:69])[CH2:65][CH2:64][O:63][CH2:62][CH2:61]1.[ClH:70]>CN(C)C=O.CC(=O)OCC.O1CCOCC1>[ClH:70].[N:60]1([CH2:66][CH2:67][CH2:68][NH:69][C:1]([C:4]2[CH:26]=[CH:25][C:7]3[NH:8][C:9](=[C:11]([C:15]4[N:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][N:16]=4)[C:12]([NH2:14])=[O:13])[NH:10][C:6]=3[CH:5]=2)=[O:3])[CH2:65][CH2:64][O:63][CH2:62][CH2:61]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 61055N-(3-Aminopropyl)morpholineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 665934042-[5-carboxy-1H-benzimidazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide

Product 1

HCID 66593309HCID 66593309, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a room temperature solution of 2-[5-carboxy-1H-benzimidazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide (630 mg, 1.73 mmol) in dimethylformamide (20 mL) was added DIPEA (661 μL, 3.79 mmol, 2.2 eq.), HBTU (720 mg, 1.90 mmol, 1.1 eq.). After 5 min, 3-(4-morpholinyl)propan-1-amine (277 μL, 1.90 mmol, 1.1 eq.) was added and the mixture was stirred at room temperature for 3 hr. The mixture was diluted with EA (50 mL) and washed three times with 5% aqueous sodium bicarbonate (50 mL each). The EA fraction was decanted, dried over magnesium sulfate, filtered, and concentrated under vacuum to give a yellow solid. About 2 mL of 4.0 M hydrogen chloride in dioxane was added, and the mixture was stirred for 15 min and then concentrated under vacuum to give 2-(5-{[3-(4-morpholinyl)propyl]aminocarbonyl}-1H-benzimidazol-2(3H)-ylidene)-2-(4-trifluoromethylpyrimidin-2-yl)acetamide hydrochloride (750 mg, 1.52 mmol, 88% yield) as a yellow solid.

Workup

  1. washwashed three times with 5% aqueous sodium bicarbonate (50 mL each)
  2. customThe EA fraction was decanted
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto give a yellow solid
  7. stirringthe mixture was stirred for 15 min
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8eae38c38bac47c982175b2e78f33049
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

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