Acetic Acid → HCID 86618244, compound

HRID 1159797Notes

Reaction equation

HRID 1159797 reaction equation
[CH3:1][C:2]1[N:3]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])[C:4]2[CH:5]=[CH:6][CH:7]=[C:8]([CH:11]=O)[C:9]=2[CH:10]=1.[C:22]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[CH3:1][C:2]1[N:3]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:14])=[O:15])[C:4]2[C:9]([CH:10]=1)=[C:8]([CH2:11][N:32]1[CH2:31][CH2:30][N:29]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:34][CH2:33]1)[CH:7]=[CH:6][CH:5]=2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 86618245HCID 86618245, compound2×

Product 1

HCID 86618244HCID 86618244, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
130 °C

Procedure

2-Methyl-1-(phenylsulfonyl)-1H-indole-4-carbaldehyde (94 mg, 0.3 mmol, Intermediate 47) was dissolved in THF (dry) (4 mL) before boc-piperazine (87.7 mg, 0.5 mmol) was added followed by acetic acid (188 mg, 3.1 mmol) and sodium triacetoxyborohydride (199 mg, 0.9 mmol) was added. The reaction mixture was heated in microwave for 720 s at 130° C. The solvent was evaporated, added water and DCM. Separated the phases and extracted the aqueous phase with DCM twice. The combined organic phases were dried (MgSO4) and the solvent was evaporated. The crude product was purified by preparative HPLC (30-60). Isolated 110 mg, as an oil, yield 80%. MS (ESI+) for C25H31N3O4S m/z 470 (M+H)+.

Workup

  1. additionwas added
  2. additionwas added
  3. customThe solvent was evaporated
  4. additionadded water and DCM
  5. customSeparated the phases
  6. extractionextracted the aqueous phase with DCM twice
  7. dry with materialThe combined organic phases were dried (MgSO4)
  8. customthe solvent was evaporated
  9. customThe crude product was purified by preparative HPLC (30-60)
  10. customIsolated 110 mg

Sources & evidence

ORD record
ord-52163f3834b24069ae78b5187c108268
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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