Hydrochloric Acid → HCID 11501209, compound

HRID 2240158Notes

Reaction equation

HRID 2240158 reaction equation
C1(C(C2C=CC=CC=2)=[N:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[C:19]([C:20]4[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][C@@H:29]5[CH2:33][CH2:32][O:31][CH2:30]5)[CH:21]=4)=[CH:18][CH:17]=[N:16]3)=[CH:11][CH:10]=2)C=CC=CC=1.O1CCCC1.Cl.[OH-].[Na+]>O.C(OCC)(=O)C>[CH3:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([C:19]2[N:15]([C:12]3[CH:11]=[CH:10][C:9]([NH2:8])=[CH:14][CH:13]=3)[N:16]=[CH:17][CH:18]=2)=[CH:21][C:22]=1[O:28][C@@H:29]1[CH2:33][CH2:32][O:31][CH2:30]1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86606422HCID 86606422, compound

Product 1

HCID 11501209HCID 11501209, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Into a 1-neck round-bottom flask was added N-(diphenylmethylene)-4-(5-{4-methoxy-3-[(3R)-tetrahydrofuran-3-yloxy]phenyl}-1H-pyrazol-1-yl) aniline (52.0 mg, 0.101 mmol), 1.0 mL of tetrahydrofuran, and 0.1 mL of 2.0 M aqueous HCl. The reaction was stirred at room temperature for 2 hours and 10 mL of 0.5 N HCl in water and 10 mL of a 2:1 mixture of hexanes and ethyl acetate were added. The clear aqueous layer was basified with 1 N NaOH and extracted with 3×10 mL of ethyl acetate. The combined organic fractions were dried over sodium sulfate and concentrated under reduced pressure to yield 4-(5-{4-methoxy-3-[(3R)-tetrahydrofuran-3-yloxy]phenyl}-1H-pyrazol-1-yl)aniline (28 mg, 79%) as a tan solid. LC/MS (EI) tR 3.11 (Method C), m/z 352.1 (M++1)

Workup

  1. additionwere added
  2. extractionextracted with 3×10 mL of ethyl acetate
  3. dry with materialThe combined organic fractions were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4a416e2fe7dd470280c366437eaae286
Source dataset
uspto-grants-2010_05
Patent number
US07723348B2

Reaction notes

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