Pyridine → HCID 70882502, compound

HRID 2234979Notes

Reaction equation

HRID 2234979 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][C@H:12]([CH3:14])[N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:10]([CH3:22])[CH2:9]2)[CH:5]=[CH:4][C:3]=1[O:23][CH3:24].N1C=CC=CC=1.[Br:31][C:32]1[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[C:34]([Cl:42])[CH:33]=1>C(Cl)Cl>[Br:31][C:32]1[CH:37]=[CH:36][C:35]([S:38]([NH:1][C:2]2[N:7]=[C:6]([N:8]3[CH2:9][C@H:10]([CH3:22])[N:11]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[C@H:12]([CH3:14])[CH2:13]3)[CH:5]=[CH:4][C:3]=2[O:23][CH3:24])(=[O:39])=[O:40])=[C:34]([Cl:42])[CH:33]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27347664-Bromo-2-chlorobenzenesulfonyl chlorideHCID 58988133HCID 58988133, compound

Product 1

HCID 70882502HCID 70882502, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,1-Dimethylethyl (2R,6S)-4-[6-amino-5-(methyloxy)-2-pyridinyl]-2,6-dimethyl-1-piperazinecarboxylate (D12)(1.0 g, 2.97 mmol) was dissolved in DCM (10 mL) and pyridine (10 mL) and then cooled to 0° C. 4-Bromo-2-chlorobenzenesulfonyl chloride (0.946 g, 3.27 mmol), dissolved in DCM (5 mL) was then added dropwise and the reaction then allowed to warm to rt overnight. The reaction was then evaporated to a minimum and redissolved in DCM (100 mL) and washed with water (50 mL). Aqueous layer was extracted with DCM (2×50 mL) and combined organic extracts washed with brine (100 mL). The organic layer was dried (MgSO4) and evaporated to give a dark oil which was purified by chromatography [silica gel, eluting with 0 to 50% Ethyl acetate/pentane]. Product fractions evaporated to give a yellow crunchy foam (D13) (1.29 g), MS (ES+) m/e 589/591 [M+H]+.

Workup

  1. additionwas then added dropwise
  2. customthe reaction
  3. customThe reaction was then evaporated to a minimum
  4. dissolutionredissolved in DCM (100 mL)
  5. washwashed with water (50 mL)
  6. extractionAqueous layer was extracted with DCM (2×50 mL)
  7. washcombined organic extracts washed with brine (100 mL)
  8. dry with materialThe organic layer was dried (MgSO4)
  9. customevaporated
  10. customto give a dark oil which
  11. customwas purified by chromatography [silica gel, eluting with 0 to 50% Ethyl acetate/pentane]
  12. customProduct fractions evaporated
  13. customto give a yellow crunchy foam (D13) (1.29 g), MS (ES+) m/e 589/591 [M+H]+

Sources & evidence

ORD record
ord-8154c716e7e34bc68a8d81fc6415fdc6
Source dataset
uspto-grants-2010_05
Patent number
US07713978B2

Reaction notes

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