Pyridine → HCID 69630494, compound

HRID 1161989Notes

Reaction equation

HRID 1161989 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31](Cl)(=[O:33])=[O:32].N1C=CC=CC=1>C(Cl)Cl>[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31]([NH:1][C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1)(=[O:33])=[O:32]

Participants

5

Reactant 3

HCID 1049PyridineHCID 761872-Chlorobenzenesulfonyl chlorideHCID 21864857HCID 21864857, compound2×

Product 1

HCID 69630494HCID 69630494, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(5-amino-1-benzofuran-7-yl)piperazine-1-carboxylate (0.59 g, 1.87 mmol; Intermediate 10) was dissolved in DCM. 2-Chlorobenzenesulfonyl chloride (0.59 g, 2.8 mmol) was added followed by pyridine (0.45 mL, 5.6 mmol). The reaction mixture was stirred at room temperature overnight. Filtration through a silica plug afforded 0.66 g (72%) of the title product. HPLC purity 92%, RT=2.56 min (System A; 10-97% MeCN over 3 min). 1H NMR (400 MHz, CDCl3) δ ppm 1.48 (s, 9H) 3.07-3.21 (m, 4H) 3.51-3.65 (m, 4H) 6.51 (d, J=2.0 Hz, 1H) 6.62 (d, J=2.3 Hz, 1H) 6.93 (d, J=2.0 Hz, 1H) 7.00 (s, 1H) 7.18-7.31 (m, 2H) 7.36-7.47 (m, 1H) 7.47-7.57 (m, 2H) 7.90 (dd, J=7.9, 1.6 Hz, 1H). MS (ESI+) m/z 492.2 (M+H)+.

Workup

  1. filtrationFiltration through a silica plug

Sources & evidence

ORD record
ord-c1051c324e8f42c5a1a565f9020629ee
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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