Benzenesulfonyl chloride → HCID 10305305, compound

HRID 970935Notes

Reaction equation

HRID 970935 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]([CH:21]1[C:30]2[N:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH2:24][CH2:23][CH2:22]1)[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][NH2:20])=[CH:15][CH:14]=1.[C:31]1([S:37](Cl)(=[O:39])=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CCN([CH2:46][CH3:47])CC>C(Cl)Cl>[C:31]1([S:37]([N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[C:2]2[CH2:10][N:11]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][NH:20][S:37]([C:47]3[CH:46]=[CH:33][CH:32]=[CH:31][CH:36]=3)(=[O:39])=[O:38])=[CH:17][CH:18]=2)[CH:21]2[C:30]3[N:29]=[CH:28][CH:27]=[CH:26][C:25]=3[CH2:24][CH2:23][CH2:22]2)(=[O:39])=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 21985008N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amine

Product 1

HCID 10305305HCID 10305305, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (302 mg, 0.760 mmol), benzenesulfonyl chloride (0.12 mL, 0.94 mmol), and Et3N (0.15 mL, 1.1 mmol) in CH2Cl2 (7.5 mL) was heated at reflux for 17 h, then concentrated in vacuo. The residue was partitioned between saturated NaHCO3(aq) (15 mL) and EtOAc (20 mL). The aqueous phase was extracted with EtOAc (20 mL), and the combined organic phases were dried (MgSO4), filtered and concentrated in vacuo. Purification of the crude material by column chromatography on silica gel (400:5:1 CH2Cl2/MeOH/NH4OH) afforded AMD9830 (229 mg, 71%) as a yellow foam. 1H NMR (CDCl3) δ 1.64-2.03 (m, 3H), 2.37 (m, 1H), 2.66-2.84 (m, 2H), 3.76-3.89 (m, 4H), 4.06 (m, 1H), 4.41 (dd, 1H, J=9.6, 6.0 Hz), 4.66 (d, 1H, J=15 Hz), 4.79 (d, 1H, J=15 Hz), 6.76 (d, 2H, J=8.1 Hz), 7.07 (m, 1H), 7.18 (d, 2H, J=8.1 Hz, 7.27 (m, 2H), 7.41 (m, 3H), 7.55 (m, 5H), 7.84 (m, 3H), 7.96 (m, 2H), 8.48 (m, 1H); 13C NMR (CDCl3) δ 20.15, 27.15, 27.55, 45.30, 51.78, 53.32, 61.49, 111.81, 118.60, 119.84, 122.59, 123.06, 125.43, 125.60, 127.06, 127.47, 127.76, 131.01, 131.24, 131.92, 132.55, 132.69, 134.81, 136.75, 138.13, 139.21, 140.14, 145.11, 151.74, 156.99. ES-MS m/z 678 (M+H). Anal. Calcd. for C37H35N5S2O4.0.5H2O: C, 64.70; H, 5.28; N, 10.20. Found: C, 64.65; H, 5.11; N, 10.08.

Workup

  1. temperatureat reflux for 17 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between saturated NaHCO3(aq) (15 mL) and EtOAc (20 mL)
  4. extractionThe aqueous phase was extracted with EtOAc (20 mL)
  5. dry with materialthe combined organic phases were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude material by column chromatography on silica gel (400:5:1 CH2Cl2/MeOH/NH4OH)
  9. customafforded AMD9830 (229 mg, 71%) as a yellow foam

Sources & evidence

ORD record
ord-d3be06b4a8274c378e8129f11c4d39f2
Source dataset
uspto-grants-2007_12
Patent number
US07312234B2

Reaction notes

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