Acetic Acid → HCID 24831471, compound

HRID 1435117Notes

Reaction equation

HRID 1435117 reaction equation
[CH3:1][O:2][C:3]1[C:37]([O:38][CH3:39])=[CH:36][C:6]2[N:7]([C:10]3[S:14][C:13]([C:15]([NH2:17])=[O:16])=[C:12]([O:18][C@@H:19]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23](NCC5CCNCC5)[C:22]=4[Cl:35])[CH3:20])[CH:11]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1.C=O.[C:42]([OH:45])(=O)[CH3:43].C(O[BH-](O[C:56](=O)[CH3:57])OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CO>[CH3:1][O:2][C:3]1[C:37]([O:38][CH3:39])=[CH:36][C:6]2[N:7]([C:10]3[S:14][C:13]([C:15]([NH2:17])=[O:16])=[C:12]([O:18][C@@H:19]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([O:45][CH2:42][CH:43]5[CH2:57][CH2:56][N:7]([CH3:8])[CH2:6][CH2:5]5)[C:22]=4[Cl:35])[CH3:20])[CH:11]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 24830190HCID 24830190, compound

Product 1

HCID 24831471HCID 24831471, compoundYield 1,116.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-[5,6-bis(methyloxy)-1H-benzimidazol-1-yl]-3-[((1R)-1-{2-chloro-3-[(4-piperidinylmethyl)amino]phenyl}ethyl)oxy]-2-thiophenecarboxamide (Example 40, 86 mg, 0.015 mmol) in 2 mL of DCM and 1 mL of MeOH was added formaldehyde (23 μl, 0.30 mmol) and acetic acid (10 μl, 0.18 mmol). After 10 min, sodium triacetoxyborohydride (49 mg, 0.23 mmol) was added and the reaction was stirred for 16 h. The solution was diluted with DCM and washed with saturated NaHCO3 solution and water, dried over MgSO4 and concentrated to give 49 mg of the title compound (56%). 1H NMR (400 MHz, d6-DMSO) δ 8.31 (s, 1H), 7.78 (br s, 1H), 7.28 (s, 1H), 7.13 (t, J=7.8 Hz, 1H), 7.07 (br s, 1H), 7.01-7.00 (m, 2H), 6.76 (d, J=7.6 Hz, 1H), 6.60 (d, J=8.0 Hz, 1H), 5.92 (m, 1H), 5.39 (m, 1H), 3.77 (s, 3H), 3.74 (s, 3H), 2.95 (m, 2H), 2.65 (m, 2H), 2.06 (s, 3H), 1.70-1.56 (m, 7H), 1.12-1.09 (m, 2H). HRMS calculated C29H34ClN5O4S [M+H]+ 584.2098, found 584.2093.

Workup

  1. washwashed with saturated NaHCO3 solution and water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e513824e8eb74479ae8b9483869ade5c
Source dataset
uspto-grants-2009_11
Patent number
US07615643B2

Reaction notes

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