Acetic Acid → N-Benzyl-N-(3,4-dimethoxy-phenyl)-4-{4-[2-hydroxy-3-(2-oxo-2,3-dihydro-1H-benzoimidazol-4-yloxy)-propylamino]-piperidin-1-yl}-benzenesulfonamide

HRID 351692Notes

Reaction equation

HRID 351692 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][CH2:16][C@H:17]([OH:30])[CH2:18][O:19][C:20]1[C:28]2[NH:27][C:26](=[O:29])[NH:25][C:24]=2[CH:23]=[CH:22][CH:21]=1.[CH2:31]([N:38]([C:55]1[CH:60]=[CH:59][C:58]([O:61][CH3:62])=[C:57]([O:63][CH3:64])[CH:56]=1)[S:39]([C:42]1[CH:47]=[CH:46][C:45]([N:48]2[CH2:53][CH2:52][C:51](=O)[CH2:50][CH2:49]2)=[CH:44][CH:43]=1)(=[O:41])=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(O)(=O)C>CN(C)C=O>[CH2:31]([N:38]([C:55]1[CH:60]=[CH:59][C:58]([O:61][CH3:62])=[C:57]([O:63][CH3:64])[CH:56]=1)[S:39]([C:42]1[CH:43]=[CH:44][C:45]([N:48]2[CH2:49][CH2:50][CH:51]([NH:15][CH2:16][CH:17]([OH:30])[CH2:18][O:19][C:20]3[C:28]4[NH:27][C:26](=[O:29])[NH:25][C:24]=4[CH:23]=[CH:22][CH:21]=3)[CH2:52][CH2:53]2)=[CH:46][CH:47]=1)(=[O:41])=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 107991054-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-oneHCID 11488488N-Benzyl-N-(3,4-dimethoxy-phenyl)-4-(4-oxo-piperidin-1-yl)-benzenesulfonamide

Product 1

HCID 10283442N-Benzyl-N-(3,4-dimethoxy-phenyl)-4-{4-[2-hydroxy-3-(2-oxo-2,3-dihydro-1H-benzoimidazol-4-yloxy)-propylamino]-piperidin-1-yl}-benzenesulfonamideYield 30.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium Triacetoxyborohydride (0.015 g, 0.72 mM) was added to a solution of 4-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydro-benzoimidazol-2-one(0.08 g, 0.36 mM), N-Benzyl-N-(3,4-dimethoxy-phenyl)-4-(4-oxo-piperidin-1-yl)-benzenesulfonamide(0.19 g, 0.39 mM), and acetic acid(0.025 ml, 0.43 mM) in anhydrous dimethylforamide(5 ml). The reaction was stirred overnight. The reaction was quenched with 50% H2O/sat. NaHCO3aq. (20 ml). The solids were captured on a filter and washed with ethyl acetate, diethyl ether, and hexanes to afford 0.075 g of the desired product as a brown solid. 1H NMR (DMSO) δ 1.31 (m, 2H), 1.89 (m, 2H), 2.71 (m, 2H), 2.87 (m, 3H), 3.53(s, 3H), 3.67 (s, 3H), 3.87 (m, 4H), 3.98 (m, 1H), 4.67(s, 2H), 4.95(bs, 1H), 6.44 (s, 1H), 6.59(m, 2H), 6.79 (m, 2H), 7.05 (d, 2H, J=8.7 Hz), 7.25 (m, 6H), 7.41(d, 2H, J=8.4 Hz), 10.59 (bs, 1H), 10.72 (bs, 1H); MS (ES) m/z: 688.1 (MH+); HRMS for C36H41N5O7S: 688.2799 (MH+)

Workup

  1. customThe reaction was quenched with 50% H2O/
  2. filtrationa filter
  3. washwashed with ethyl acetate, diethyl ether, and hexanes

Sources & evidence

ORD record
ord-ed198f8e8be64de2a8ea50d9eeb1a145
Source dataset
uspto-grants-2004_06
Patent number
US06743787B2

Reaction notes

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