Hydrochloric Acid → HCID 86724134, compound

HRID 1748805Notes

Reaction equation

HRID 1748805 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:15]2[C:16]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=3)=[N:17][N:18]([CH2:28][CH3:29])[C:19]=2[NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:10][CH:11]=[CH:12][O:13]C)=[CH:5][CH:4]=1.C([O-])(O)=O.[Na+]>C1COCC1>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([C:15]2[C:16]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=3)=[N:17][N:18]([CH2:28][CH3:29])[C:19]=2[NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:10][CH2:11][CH:12]=[O:13])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86724133HCID 86724133, compound

Product 1

HCID 86724134HCID 86724134, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2 M aqueous hydrogen chloride (1.00 mL, 2.00 mmol) was added in one portion to a solution of tert-butyl (4-(1-(4-bromophenyl)-4-methoxybut-3-en-1-yl)-1-ethyl-3-(pyridin-2-yl)-1H-pyrazol-5-yl)carbamate (0.0708 g, 0.118 mmol) and THF (2.00 mL) under air. After about 45 min, 5 mL saturated aqueous NaHCO3 (5 mL) was added. The mixture was extracted with EtOAc (2×5 mL). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified on silica gel using a gradient of 0-50% EtOAc in heptane. The fractions containing product were combined and concentrated under reduced pressure to afford tert-butyl (4-(1-(4-bromophenyl)-4-oxobutyl)-1-ethyl-3-(pyridin-2-yl)-1H-pyrazol-5-yl)carbamate (0.0450 g, 0.0880 mmol, 74%) as a sticky, pale yellow solid. LC-MS (Table 1, Method g) Rt=2.72 min; m/z 513 and 515 (M+H)+.

Workup

  1. extractionThe mixture was extracted with EtOAc (2×5 mL)
  2. dry with materialThe combined organics were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified on silica gel using a gradient of 0-50% EtOAc in heptane
  6. additionThe fractions containing product
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-85ab52eb33db4da6a08ae3dbc352e4ca
Source dataset
uspto-grants-2015_10
Patent number
US09150592B2

Reaction notes

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