Benzenesulfonyl chloride → HCID 25125207, compound

HRID 1645254Notes

Reaction equation

HRID 1645254 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH:22]3[CH2:24][CH2:23]3)=[N:9][C:10]=2[C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH2:21])[CH:15]=2)=[O:12])[CH:5]=[CH:6][N:7]=1.C(N(CC)CC)C.[C:32]1([S:38](Cl)(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(CC1C=C(CN(C)C)C(O)=C(CN(C)C)C=1)C.O>[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH:22]3[CH2:24][CH2:23]3)=[N:9][C:10]=2[C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][S:38]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)(=[O:40])=[O:39])[CH:15]=2)=[O:12])[CH:5]=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 66775481HCID 66775481, compound

Product 1

HCID 25125207HCID 25125207, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 70262,4,6-Tris((dimethylamino)methyl)phenolSolvent

Procedure

A solution of EXAMPLE 68A (0.102 g) in DMF 3 mL was treated with triethylamine (0.112 ml, 0.800 mmol) and benzenesulfonyl chloride (0.026 ml, 0.200 mmol), stirred at room temperature overnight then diluted with water and extracted with ethyl acetate. The extract was washed (brine), dried (MgSO4), concentrated to dryness and purified by preparative HPLC. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.01-1.29 (m, 4H) 2.34-2.58 (m, 1H) 3.98 (d, J=5.95 Hz, 2H) 7.04 (d, J=7.54 Hz, 1H) 7.19-7.36 (m, 2H) 7.48-7.69 (m, 4H) 7.72 (s, 1H) 7.77-7.91 (m, 2H) 7.98 (d, J=5.55 Hz, 1H) 8.18 (t, J=6.35 Hz, 1H) 9.08 (s, 1H) 10.32 (s, 1H) 10.69 (s, 1H). MS (ESI(+)) m/e 463 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed (brine)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to dryness
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-b7d7b4640d6949bbb75d4e8fcab1aef8
Source dataset
uspto-grants-2012_02
Patent number
US08124759B2

Reaction notes

Loading…