Pyridine → HCID 131726140, compound

HRID 856929Notes

Reaction equation

HRID 856929 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:22]3[O:21][CH:20]=[CH:19][C:18]=3[CH:17]=[C:16]([NH2:23])[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30]([Cl:33])(=[O:32])=[O:31])=[CH:26][CH:25]=1.N1C=CC=CC=1>ClCCl>[ClH:33].[CH3:34][C:24]1[CH:29]=[CH:28][C:27]([S:30]([NH:23][C:16]2[CH:15]=[C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[C:22]3[O:21][CH:20]=[CH:19][C:18]=3[CH:17]=2)(=[O:32])=[O:31])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 21864857HCID 21864857, compound

Product 1

HCID 131726140HCID 131726140, compoundYield 17.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(5-Amino-benzofuran-7-yl)-piperazine-1-carboxylic acid tert-butyl ester (44 mg, 0.139 mmol) in 3 ml dichloromethane was added to a tube containing p-toluenesulfonyl chloride (32 mg, 0.167 mmol) together with pyridine (100 μl, 1.25 mmol) and left on a shaker over weekend. After purification by preparative HPLC, the resulting Boc-material was treated with HCl in ether and left on a shaker until the salt had formed. The solution was centrifugated and the supernatant was removed. Ether was added, then centrifugated and decanted (repeated three times) to remove the excess HCl. The remaining ether was finally evaporated in a SpeedVAc concentrator to yield 10 mg of title product. HPLC purity=94%, m/z=372.3 (M+H). 1H NMR (270 MHz, methanol-d4) δ ppm 2.35 (s, 3 H) 3.45 (m, 8 H) 6.63 (d, J=1.85 Hz, 1 H) 6.71 (d, J=2.11 Hz, 1 H) 6.88 (d, J=1.85 Hz, 1 H) 7.25 (m, 2 H) 7.58 (m, 2 H) 7.71 (d, J=2.11 Hz, 1 H).

Workup

  1. waitleft on a shaker over weekend
  2. customAfter purification by preparative HPLC
  3. additionthe resulting Boc-material was treated with HCl in ether
  4. waitleft on a shaker until the salt
  5. customhad formed
  6. customthe supernatant was removed
  7. additionEther was added
  8. customdecanted (repeated three times)
  9. customto remove the excess HCl
  10. customThe remaining ether was finally evaporated in a SpeedVAc concentrator

Sources & evidence

ORD record
ord-1f8686a072344b79877d8357de089cd7
Source dataset
uspto-grants-2006_12
Patent number
US07144883B2

Reaction notes

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