Pyridine → HCID 69626822, compound

HRID 1161977Notes

Reaction equation

HRID 1161977 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12]1[CH:13]=[C:14]([N:21]([CH3:34])[CH2:22][CH2:23][CH2:24][N:25]([CH3:33])[C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:15]2[O:19][CH:18]=[CH:17][C:16]=2[CH:20]=1.N1C=CC=CC=1>C(Cl)Cl>[CH3:33][N:25]([CH2:24][CH2:23][CH2:22][N:21]([CH3:34])[C:14]1[C:15]2[O:19][CH:18]=[CH:17][C:16]=2[CH:20]=[C:12]([NH:11][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH:13]=1)[C:26](=[O:32])[O:27][C:28]([CH3:30])([CH3:31])[CH3:29]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 66899833HCID 66899833, compound2×

Product 1

HCID 69626822HCID 69626822, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzenesulfonyl chloride (115 μL, 0.9 mmol) was added to a mixture of tert-butyl 3-[(5-amino-1-benzofuran-7-yl)(methyl)amino]propyl(methyl)carbamate (Intermediate 2; 250 mg, 0.75 mmol) in DCM (2 mL) followed by addition of pyridine (1 mL). The reaction mixture was stirred at room temperature for 4 h. The volatiles were evaporated in vacuo and the residue obtained was purified using RP-HPLC (Gilson/YMC AQ C18; 150×30 mm) to give the title compound as a beige oil (202 mg, 43% over 4 steps); HPLC 93%, RT: 2.49 min (System A); 95%, RT: 2.27 min (System B); 1H NMR (CDCl3) δ ppm 1.41 (s, 9H), 1.60-1.75 (m, 2H), 2.74 (s, 3H), 2.93 (s, 3H), 3.13-3.25 (m, 2H), 3.42-3.53 (m, 2H), 6.19-6.69 (m, 2H), 6.87-7.06 (m, 1H), 7.33-7.58 (m, 4H), 7.71-7.79 (m, 2H); MS m/z 474 (M+H)+.

Workup

  1. customThe volatiles were evaporated in vacuo
  2. customthe residue obtained
  3. customwas purified

Sources & evidence

ORD record
ord-8459e5ba2a75430ea67d86d5d39a5e4f
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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