Acetic Acid → HCID 69655116, compound

HRID 1061423Notes

Reaction equation

HRID 1061423 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.[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH:52]=[CH:53][C:54]=1[O:55][CH3:56])[C:36]([NH:38][C:39]1[CH:44]=[CH:43][C:42]([N:45]2[CH2:50][CH2:49][C:48](=O)[CH2:47][CH2:46]2)=[CH:41][CH:40]=1)=[O:37].C(O)(=O)C>CN(C)C=O>[OH:30][C@H:17]([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)[CH2:16][NH:15][CH:48]1[CH2:47][CH2:46][N:45]([C:42]2[CH:43]=[CH:44][C:39]([NH:38][C:36](=[O:37])[C:35]3[CH:52]=[CH:53][C:54]([O:55][CH3:56])=[C:33]([O:32][CH3:31])[CH:34]=3)=[CH:40][CH:41]=2)[CH2:50][CH2:49]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 107991054-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-oneHCID 22220340HCID 22220340, compound

Product 1

HCID 69655116HCID 69655116, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium triacetoxyborohydride (0.044 g, 2.1 mmol) was added to a solution of 4-((2S)-3-amino-2-hydroxy-propoxy)-1,3-dihydro-benzoimidazol-2-one (U.S. Pat. No. 5,786,356) (0.23 g, 1.05 mmol), 3,4-dimethoxy-N-[4-(4-oxo-piperidine-1-yl)-phenyl]-benzamide (which was obtained in Example 369) (0.41 g, 1.16 mmol), and acetic acid (0.07 mL, 1.16 mmol) in anhydrous dimethylforamide (8 mL). The reaction was stirred for 2 hours. The reaction was quenched with 50% water/saturated aqueous NaHCO3(20 mL). The solids were captured on a filter and washed with ethyl acetate, diethyl ether, and hexanes to afford 0.31 g of the desired product as a brown solid; 1H NMR (300 MHz, DMSO-d6) δ 1.32 (m, 2H), 1.89 (m, 2H), 2.54 (m, 1H), 2.65 (m, 2H), 2.84 (m, 2H), 3.56 (m, 2H), 3.83 (s, 3H), 3.84 (s, 3H), 3.95 (m, 2H), 4.02 (s, 1H), 5.06 (brs, 1H), 6.52 (d, 1H, J=7.1), 6.51 (d, 1H, J=8.1Hz), 6.88 (m, 2H), 7.08 (d, 1H, J=8.7 Hz), 7.58 (m, 5H), 8.87 (s, 1H), 10.59 (brs, 1H), 10.72 (brs, 1H); MS (ES) m/z: 561.2 (MH+).

Workup

  1. customThe reaction was quenched with 50% water/saturated aqueous NaHCO3(20 mL)
  2. filtrationa filter
  3. washwashed with ethyl acetate, diethyl ether, and hexanes

Sources & evidence

ORD record
ord-63cd134bd85742c7a9d0a63f62b2fe9d
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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