Triethylamine → HCID 67272498, compound

HRID 1592456Notes

Reaction equation

HRID 1592456 reaction equation
[C:1]([O:5][C:6](=[O:30])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:21][C:22]1[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][N:23]=1)[CH2:13][C:14]1[C:19]([OH:20])=[CH:18][CH:17]=[CH:16][N:15]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:31][N:32]([CH3:37])[S:33](Cl)(=[O:35])=[O:34].CCN(CC)CC>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6](=[O:30])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:21][C:22]1[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][N:23]=1)[CH2:13][C:14]1[C:19]([O:20][S:33](=[O:35])(=[O:34])[N:32]([CH3:37])[CH3:31])=[CH:18][CH:17]=[CH:16][N:15]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 67272764HCID 67272764, compound

Product 1

HCID 67272498HCID 67272498, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of {4-[(3,5-dimethyl-pyridin-2-ylmethyl)-(3-hydroxy-pyridin-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester (0.190 g, 0.46 mmol) in CH2Cl2 (4 mL) was added dimethylsulfamoylchloride (0.160 mL, 1.49 mmol), NEt3 (0.300 g, 2.16 mmol) and DMAP (catalytic) and the reaction mixture stirred for 48 h. The mixture was diluted with CH2Cl2 (30 mL) and the organic layer was washed with saturated aqueous NaHCO3 (2×30 mL), dried (MgSO4), and concentrated. Purification by column chromatography on silica gel with saturated NH4OH in Et2O afforded {4-[(3,5-dimethyl-pyridin-2-ylmethyl)-(3-dimethylsulfamoyloxy-pyridin-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester (0.054 g, 23%) 1H NMR (CDCl3) δ 1.30-1.53 (m, 13H), 2.11 (s, 3H), 2.25 (s, 3H), 2.50-2.54 (m, 2H), 2.94-3.00 (m, 8H), 3.74 (s, 2H), 3.91 (s, 2H), 5.11 (br s, 1H), 7.16 (s, 1H), 7.23 (dd, 1H, J=6.6, 4.8 Hz), 7.72 (d, 1H, J=8.3 Hz), 8.13 (s, 1H), 8.51 (d, 1H, J=4.1 Hz).

Workup

  1. washthe organic layer was washed with saturated aqueous NaHCO3 (2×30 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customPurification by column chromatography on silica gel with saturated NH4OH in Et2O

Sources & evidence

ORD record
ord-1c408e942afd475bbf8f53cb86590e29
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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