Ammonia → HCID 24803238, compound

HRID 1698067Notes

Reaction equation

HRID 1698067 reaction equation
[N+]([C:4]1[CH:31]=[CH:30][C:7]2[N:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([N:17]4[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]4)=[N:15][CH:16]=3)[S:10][C:6]=2[CH:5]=1)([O-])=O.N.[CH3:33][OH:34]>[Pd]>[CH3:33][O:34][C:4]1[CH:31]=[CH:30][C:7]2[N:8]=[C:9]([C:11]3[CH:16]=[N:15][C:14]([N:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)=[CH:13][CH:12]=3)[S:10][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 887Methanol2×HCID 57553414HCID 57553414, compound

Product 1

HCID 24803238HCID 24803238, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

tert-Butyl 4-[5-(6-nitro-1,3-benzothiazol-2-yl)pyridin-2-yl]piperazine-1-carboxylate (90 mg, 0.2 mmol) was dissolved in methanol (8 mL). After addition of 7M NH3 in methanol (2 mL), palladium on carbon (10%, 10 mg) was added and the flask was evacuated and filled with hydrogen gas. The reaction mixture was shaken under an atmosphere of hydrogen overnight. The mixture was thereafter filtered through diatomaceous earth and evaporated in vacuo. The crude product was purified by flash column chromatography (heptane:ethyl acetate; 70:30 to 35:65), to give the title compound (38 mg) as a solid. MS m/z (M+H) 412.

Workup

  1. additionwas added
  2. customthe flask was evacuated
  3. additionfilled with hydrogen gas
  4. filtrationThe mixture was thereafter filtered through diatomaceous earth
  5. customevaporated in vacuo
  6. customThe crude product was purified by flash column chromatography (heptane:ethyl acetate; 70:30 to 35:65)

Sources & evidence

ORD record
ord-1028bac07b774f5697331cd08ee7fc00
Source dataset
uspto-grants-2012_04
Patent number
US08163928B2

Reaction notes

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