Pyridine → HCID 66894250, compound

HRID 1162025Notes

Reaction equation

HRID 1162025 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[S:10]([Cl:13])(=[O:12])=[O:11].[N:14]1C=CC=CC=1.C(OC(=O)N[CH:27]1[CH2:32][CH2:31][N:30]([C:33]2[C:41]3[O:40][CH:39]=[CH:38][C:37]=3[CH:36]=[C:35]([NH2:42])[CH:34]=2)[CH2:29][CH2:28]1)(C)(C)C>C(Cl)Cl>[ClH:13].[NH2:14][CH:31]1[CH2:32][CH2:27][CH2:28][CH2:29][N:30]1[C:33]1[C:41]2[O:40][CH:39]=[CH:38][C:37]=2[CH:36]=[C:35]([NH:42][S:10]([C:4]2[CH:5]=[C:6]([CH3:9])[CH:7]=[CH:8][C:3]=2[O:2][CH3:1])(=[O:12])=[O:11])[CH:34]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 1451496-Methoxy-m-toluenesulfonyl chlorideHCID 86609637HCID 86609637, compound2×

Product 1

HCID 66894250HCID 66894250, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methoxy-5-methylbenzenesulfonyl chloride (80.0 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 59.0 mg (47%) of the title product. HPLC 100%, RT: 1.731 (System A; 10-97% MeCN over 3 min). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.70-1.76 (m, 2H) 2.05 (d, J=10.05 Hz, 2H) 2.20 (s, 3H) 2.76 (t, J=11.46 Hz, 2H) 3.19-3.21 (m, 1H) 3.65 (d, J=12.56 Hz, 2H) 3.87 (s, 3H) 6.58 (d, J=1.88 Hz, 1H) 6.81 (d, J=2.20 Hz, 1H) 6.89 (d, J=1.88 Hz, 1H) 7.04 (d, J=8.48 Hz, 1H) 7.32 (dd, J=8.48, 2.20 Hz, 1H) 7.51 (d, J=2.20 Hz, 1H) 7.86 (d, J=1.88 Hz, 1H) 8.35 (d, J=3.45 Hz, 3H) 9.65 (s, 1H). LC-MS 416 (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-1448a6f537434cf6abfb24e97ffa14c2
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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