Piperazine → HCID 68716587, compound

HRID 1159809Notes

Reaction equation

HRID 1159809 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].FC(F)(F)C(O)=O.[CH3:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:35][N:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)=[C:21]2[C:25]=1[N:24]([S:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=[O:28])=[O:27])[CH:23]=[CH:22]2.[NH:42]1CCNC[CH2:43]1.C[Si](C#N)(C)C>CO>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([CH:35]([N:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[C:43]#[N:42])=[C:21]2[C:25]=1[N:24]([S:26]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)(=[O:28])=[O:27])[CH:23]=[CH:22]2

Participants

5

Reactant 3

HCID 4837PiperazineHCID 82115Trimethylsilyl cyanideHCID 86618252HCID 86618252, compound

Product 1

HCID 68716587HCID 68716587, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Benzenesulfonyl-7-methoxy-1H-indole-4-carbaldehyde (50 mg, 0.2 mmol, prepared as in Example 79), piperazine (28 mg, 0.3 mmol) and methanol (0.5 mL) was charged into a tube suitable for microwave irradiation. The mixture was heated at 100° for 1 min in the microwave oven. Trimethylsilyl cyanide (21 μl, 0.2 mmol) was added and the heat treatment, 100° 1 min, was repeated. LCMS indicated the formation of expected product. The crude product was purified using prep LC on a YMC column (24-52% MeCN over 16 min). Obtained 26.2 mg (40%). MS ESI+ for C16H13NO4S, m/z 325 (M-piperazine)+, m/z 384 (M-nitrile)+, m/z 411 (M+H)+.

Workup

  1. temperatureThe mixture was heated at 100° for 1 min in the microwave oven
  2. customthe heat treatment, 100° 1 min

Sources & evidence

ORD record
ord-a036f054c8854a679571cdbb0718f914
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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