Hydrochloric Acid → HCID 178464437, compound

HRID 872525Notes

Reaction equation

HRID 872525 reaction equation
[C:1]([C:4]1[CH:8]=[C:7]([C:9]([NH:11][CH2:12][CH2:13][C:14]2[O:15][C:16]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=3)=[CH:17][CH:18]=2)=[O:10])[NH:6][N:5]=1)(=O)[CH3:2].[NH2:27][CH2:28][CH2:29][OH:30].[BH4-].[Na+].Cl>C1(C)C=CC=CC=1.O.C1COCC1>[Cl:26][C:21]1[CH:20]=[C:19]([C:16]2[O:15][C:14]([CH2:13][CH2:12][NH:11][C:9]([C:7]3[NH:6][N:5]=[C:4]([CH:1]([NH:27][CH2:28][CH2:29][OH:30])[CH3:2])[CH:8]=3)=[O:10])=[CH:18][CH:17]=2)[CH:24]=[CH:23][C:22]=1[Cl:25]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 700EthanolamineHCID 4311764Sodium borohydride2×HCID 67171427HCID 67171427, compound

Product 1

HCID 178464437HCID 178464437, compoundYield 26%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Acetyl-N-(2-(5-(3,4-dichlorophenyl)furan-2-yl)ethyl)-1H-pyrazole-5-carboxamide (78 mg; 0.20 mmol) and 2-aminoethanol (10 mg; 0.17 mmol) were dissolved in 5 ml of dry toluene and 5 ml of dry THF and stirred for 6.5 h at 75° C. under nitrogen atmosphere and then overnight at RT. Sodium tetrahydroborate (18.8 mg; 0.50 mmol) was added, stirred for 3 days at RT and then 4.5 h at 75° C. 10 mg of sodium tetrahydroborate was added and the mixture was heated for 5 h at 50° C. to complete the reaction. 0.1 ml of water was added at 0° C. and pH adjusted to 1 with 1 M HCl. Solution was evaporated to dryness, 15 ml of DCM was added and the mixture was washed with 10 ml of water. pH was adjusted to 12 with 1 M NaOH and 15 ml of DCM was added. After Na2SO4 drying the compound was purified by chromatography (CombiFlash, Silica column, 2.5-10% MeOH/DCM) to obtain 19 mg (26%) of the title compound. 1H-NMR (400 MHz; d1-CDCl3): δ 1.43 (d, 3H), 2.55-2.70 (m, 1H), 2.74-2.85 (m, 1H), 2.97 (t, 2H), 3.60-3.76 (m, 4H), 4.02-4.12 (m, 1H), 6.16 (d, 1H), 6.53 (d, 1H), 6.65 (s, 1H), 7.33-7.41 (m, 3H), 7.67 (d, 1H).

Workup

  1. customovernight
  2. customat RT
  3. custom4.5 h
  4. customat 75° C
  5. temperaturethe mixture was heated for 5 h at 50° C.
  6. customthe reaction
  7. customSolution was evaporated to dryness, 15 ml of DCM
  8. additionwas added
  9. washthe mixture was washed with 10 ml of water
  10. additionwas added
  11. customAfter Na2SO4 drying the compound was purified by chromatography (CombiFlash, Silica column, 2.5-10% MeOH/DCM)

Sources & evidence

ORD record
ord-b189437a847b4493968e8a13a20cfcc4
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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