Pyridine → HCID 66893944, compound

HRID 1162023Notes

Reaction equation

HRID 1162023 reaction equation
[C:1]1([S:7]([Cl:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:11]1C=CC=CC=1.C(OC(=O)N[CH:24]1[CH2:29][CH2:28][N:27]([C:30]2[C:38]3[O:37][CH:36]=[CH:35][C:34]=3[CH:33]=[C:32]([NH2:39])[CH:31]=2)[CH2:26][CH2:25]1)(C)(C)C>C(Cl)Cl>[ClH:10].[NH2:11][CH:28]1[CH2:29][CH2:24][CH2:25][CH2:26][N:27]1[C:30]1[C:38]2[O:37][CH:36]=[CH:35][C:34]=2[CH:33]=[C:32]([NH:39][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH:31]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 86609637HCID 86609637, compound2×

Product 1

HCID 66893944HCID 66893944, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzenesulfonyl chloride (64.0 mg, 0.36 mmol) and pyridine (219 μL) 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 31.3 mg (28%) of the title product. HPLC 100%, RT: 1.612 (System A; 10-97% MeCN over 3 min). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.69-1.70 (m, 2H) 2.00-2.01 (m, 2H) 2.76 (t, J=11.30 Hz, 2H) 3.18-3.26 (m, 1H) 6.54 (d, J=1.88 Hz, 1H) 6.82 (d, J=2.20 Hz, 1H) 6.86 (d, J=1.88 Hz, 1H) 7.52 (t, J=7.54 Hz, 2H) 7.57-7.68 (m, 1H) 7.71-7.72 (m, 2H) 7.88 (d, J=2.20 Hz, 1H) 8.14 (s, 3H) 10.03 (s, 1H). LC-MS 372 (M+H)+.

Workup

  1. customsolvent was removed in vacuo
  2. customthe residue was purified by preparative HPLC
  3. additioncontaining 0.1% trifluoroacetic acid
  4. customHPLC 100%, RT
  5. wait10-97% MeCN over 3 min)

Sources & evidence

ORD record
ord-5e523f7578de403599e174594de9d22d
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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