Water → HCID 86674813, compound

HRID 1520785Notes

Reaction equation

HRID 1520785 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]3[O:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]3)=[CH:11][CH:10]=2)=[O:7])=[N:2]1.[Cl:28][C:29]1[C:34](Cl)=[N:33][CH:32]=[CH:31][N:30]=1.C(=O)([O-])[O-].[K+].[K+].O>CC(N(C)C)=O>[Cl:28][C:29]1[C:34]([N:1]2[CH:5]=[CH:4][C:3]([C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([C@@H:15]4[O:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]4)=[CH:11][CH:10]=3)=[O:7])=[N:2]2)=[N:33][CH:32]=[CH:31][N:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 785752,3-Dichloropyrazine2×HCID 178452471HCID 178452471, compound

Product 1

HCID 86674813HCID 86674813, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

(S)-tert-Butyl 2-(4-(1H-pyrazole-3-carboxamido)phenyl)morpholine-4-carboxylate (90 mg, 0.24 mmol) and 2,3-dichloropyrazine (43 mg, 0.29 mmol) were dissolved in dimethylacetamide (2 ml) and potassium carbonate (67 mg, 0.48 mmol) was added. The reaction mixture was placed on a Büchi shaker for 16 hours at 80° C. To complete the reaction an additional amount of 2,3-dichloropyrazine (10 mg) was added and heating was continued for another 2 h at 120° C. After cooling the mixture, water was added followed by extraction with ethyl acetate twice. The combined organic layers was dried over MgSO4 and evaporated. The crude material was purified by flash chromatography (silica gel, 10 g, 25% to 50% EtOAc in heptane) to yield an off-white gum (48 mg, 42%). MS (ISP): 429.3 (100%, [M−tBu+H]+), 485.4 (10%, [M+H]+).

Workup

  1. additionwas added
  2. temperatureheating
  3. waitwas continued for another 2 h at 120° C
  4. additionwas added
  5. extractionfollowed by extraction with ethyl acetate twice
  6. dry with materialThe combined organic layers was dried over MgSO4
  7. customevaporated
  8. customThe crude material was purified by flash chromatography (silica gel, 10 g, 25% to 50% EtOAc in heptane)

Sources & evidence

ORD record
ord-307916a4de264c63b3ca3b18d01d3839
Source dataset
uspto-grants-2015_07
Patent number
US09073911B2

Reaction notes

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