Hydrochloric Acid → HCID 86666037, compound

HRID 469740Notes

Reaction equation

HRID 469740 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[C:9]([C:13]1[O:17][N:16]=[C:15]([NH:18][C:19]([C@@H:21]2[CH2:25][C@@H:24]([OH:26])[CH2:23][NH:22]2)=[O:20])[CH:14]=1)([CH3:12])([CH3:11])[CH3:10].Cl.C(N(C(C)C)CC)(C)C>C(O)C>[C:9]([C:13]1[O:17][N:16]=[C:15]([NH:18][C:19]([C@@H:21]2[CH2:25][C@@H:24]([OH:26])[CH2:23][N:22]2[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)=[O:20])[CH:14]=1)([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 775312,4-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 67953452HCID 67953452, compound

Product 1

HCID 86666037HCID 86666037, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,4-Dichloropyrimidine (33.2 mg, 0.223 mmol) is added to the solution of (2S,4R)-4-Hydroxy-pyrrolidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide; hydrochloride (66 mg, 0.223 mmol) and diisopropylethylamine (0.078 mL, 0.446 mmol) in ethanol (2 mL). The reaction is stirred at room temperature overnight. The reaction is quenched with saturated sodium bicarbonate aqueous solution and extracted with ethyl acetate twice. The organics are combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by chromatography on silica eluting with methanol/dichloromethane provides the title compound. ESI m/z 366 [M+H+].

Workup

  1. customThe reaction is quenched with saturated sodium bicarbonate aqueous solution
  2. extractionextracted with ethyl acetate twice
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by chromatography on silica eluting with methanol/dichloromethane

Sources & evidence

ORD record
ord-00ef6f34a1d64eb1bdfef18ee8800780
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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