Pyridine → HCID 66893845, compound

HRID 1162024Notes

Reaction equation

HRID 1162024 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].[N:12]1C=CC=CC=1.C(OC(=O)N[CH:25]1[CH2:30][CH2:29][N:28]([C:31]2[C:39]3[O:38][CH:37]=[CH:36][C:35]=3[CH:34]=[C:33]([NH2:40])[CH:32]=2)[CH2:27][CH2:26]1)(C)(C)C>C(Cl)Cl>[ClH:1].[NH2:12][CH:29]1[CH2:30][CH2:25][CH2:26][CH2:27][N:28]1[C:31]1[C:39]2[O:38][CH:37]=[CH:36][C:35]=2[CH:34]=[C:33]([NH:40][S:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])(=[O:10])=[O:9])[CH:32]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 761872-Chlorobenzenesulfonyl chlorideHCID 86609637HCID 86609637, compound2×

Product 1

HCID 66893845HCID 66893845, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chlorobenzenesulfonyl chloride (76.0 mg, 0.36 mmol) and pyridine (219 mL) were added to tert-butyl[1-(5-amino-1-benzofuran-7-yl)piperidin-4-yl]carbamate (100.0 mg, 0.30 mmol; Intermediate 49) in DCM (1 mL). The mixture was shaken at room temperature for 1 h, solvent was removed in vacuo and the residue was purified by preparative HPLC using acetonitrile-water gradients containing 0.1% trifluoroacetic acid. N-deprotection and conversion into the hydrochloride salt was performed by treatment with 2 M HCl in ether. This furnished to 60.6 mg (50%) of the title product. HPLC 100%, RT: 1.702 (System A; 10-97% MeCN over 3 min). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.69-1.72 (m, 2H) 2.01-2.02 (m, 2H) 2.76 (t, J=11.62 Hz, 2H) 3.21 (s, 1H) 3.68 (d, J=12.56 Hz, 2H) 6.58 (s, 1H) 6.82 (d, J=2.20 Hz, 1H) 6.88 (s, 1H) 7.47 (t, J=7.54 Hz, 1H) 7.62-7.63 (m, 2H) 7.87 (d, J=1.88 Hz, 1H) 7.99 (d, J=7.54 Hz, 1H) 8.23 (s, 3H) 10.33 (s, 1H). LC-MS 406 (M+H)+.

Workup

  1. customsolvent was removed in vacuo
  2. customthe residue was purified by preparative HPLC
  3. additioncontaining 0.1% trifluoroacetic acid

Sources & evidence

ORD record
ord-9f97abbd0d6b40e6bef94edbc4b60ebd
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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