Sodium Carbonate → HCID 57430015, compound

HRID 1169839Notes

Reaction equation

HRID 1169839 reaction equation
Cl.[Br:2][C:3]1[C:4]([C:9]2([CH2:21][NH2:22])[CH2:14][CH2:13][N:12]([S:15]([CH2:18][CH2:19][CH3:20])(=[O:17])=[O:16])[CH2:11][CH2:10]2)=[N:5][CH:6]=[CH:7][CH:8]=1.C(N(CC)C(C)C)(C)C.[Cl:32][C:33]1[CH:41]=[C:40]([Cl:42])[CH:39]=[CH:38][C:34]=1[C:35](Cl)=[O:36].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[Br:2][C:3]1[C:4]([C:9]2([CH2:21][NH:22][C:35](=[O:36])[C:34]3[CH:38]=[CH:39][C:40]([Cl:42])=[CH:41][C:33]=3[Cl:32])[CH2:14][CH2:13][N:12]([S:15]([CH2:18][CH2:19][CH3:20])(=[O:16])=[O:17])[CH2:11][CH2:10]2)=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 666452,4-Dichlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 68691725HCID 68691725, compound

Product 1

HCID 57430015HCID 57430015, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{[4-(3-Bromopyridin-2-yl)-1-(propylsulfonyl)piperidin-4-yl]methyl}amine hydrochloride salt (100 mg, 0.24 mmol) was dissolved in dichloromethane (5 mL) with N,N-diisopropylethylamine (0.13 mL, 0.72 mmol). 2,4-dichlorobenzoyl chloride (34 μL, 0.24 mmol) was added and the mixture stirred over night. The mixture was poured into aqueous sodium carbonate (10 mL, 2 M) and extracted with dichloromethane (10 mL x 2). The combined organic phases were dried over magnesium sulphate (anhydrous), filtered and evaporated. The reside was purified by flash column chromatography on silica gel using dichloromethane containing 10% ethyl acetate as eluent to afford the desired product: N-{[4-(3-bromopyridin-2-yl)-1-(propylsulfonyl)piperidin-4-yl]methyl}-2,4-dichlorobenzamide: 1H NMR δ (ppm)(CDCl3): 8.50 (1 H, dd, J=1.4, 4.5 Hz), 7.94 (1 H, dd, J=1.4, 7.9 Hz), 7.58 (1 H, d, J=8.3 Hz), 7.36(1 H, d, J=1.9 Hz), 7.29 (1 H, dd, J=8.3, 1.9 Hz), 7.10 (1 H, dd, J=4.5, 7.9 Hz), 6.87 (1 H, m), 5.30 (1 H, s), 4.15 (2 H, d, J=6.2 Hz), 3.46-3.44 (4 H, m), 3.14-3.08 (2 H, m), 2.90-2.88 (2 H, m), 1.90-1.76 (4 H, m), 1.06 (3 H, t, J=7.4 Hz); m/z (ES) 548, 550 (M+H).

Workup

  1. extractionextracted with dichloromethane (10 mL x 2)
  2. dry with materialThe combined organic phases were dried over magnesium sulphate (anhydrous)
  3. filtrationfiltered
  4. customevaporated
  5. customThe reside was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-6fc61cb28c594e56bc6583b9223a7102
Source dataset
uspto-grants-2010_11
Patent number
US07825135B2

Reaction notes

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