Acetic Acid → HCID 57539110, compound

HRID 1685463Notes

Reaction equation

HRID 1685463 reaction equation
C(O)(=O)C.[NH:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[C@H:14]1[CH2:19][C@H:18]([NH:20][C:21]([C:23]2[CH:32]=[CH:31][C:26]3[O:27][CH2:28][CH2:29][O:30][C:25]=3[CH:24]=2)=[O:22])[CH2:17][CH2:16][NH:15]1.C(O[C:36]1(O[Si](C)(C)C)[CH2:38][CH2:37]1)C.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO.C(OCC)(=O)C>[NH:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[C@H:14]1[CH2:19][C@H:18]([NH:20][C:21]([C:23]2[CH:32]=[CH:31][C:26]3[O:27][CH2:28][CH2:29][O:30][C:25]=3[CH:24]=2)=[O:22])[CH2:17][CH2:16][N:15]1[CH:36]1[CH2:38][CH2:37]1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 57538969HCID 57538969, compound

Product 1

HCID 57539110HCID 57539110, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acetic acid (0.075 mL, 1.3 mmol) was added to a solution of N-((2R,4R)-2-(1H-benzo[d]imidazol-2-yl)piperidin-4-yl)-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamide (50 mg, 0.13 mmol) in methanol (2 mL) and the then (1-ethoxycyclopropoxy)trimethylsilane (138 mg, 1.79 mmol) was added to the reaction solution and reaction mixture was stirred at room temperature for 10 min, then sodium cyanoborohydride (37 mg, 0.59 mmol) was added carefully. The reaction mixture was stirred at 50° C. 24 hours. Saturated sodium bicarbonate solution (10 mL) and ethyl acetate (30 mL) were added. The organic layer was separated, dried over MgSO4, and concentrated. Product was purified by Companion (ReadySep, 12 g, silica gel packed) with CH3OH/CH2Cl2 from 1%-5% to give the named compound as a white solid 46 mg (85%). LC-MS: 419.2, 417.3 (t=1.7 min).

Workup

  1. stirringThe reaction mixture was stirred at 50° C
  2. custom24 hours
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customProduct was purified by Companion (ReadySep, 12 g, silica gel packed) with CH3OH/CH2Cl2 from 1%-5%

Sources & evidence

ORD record
ord-f16e43412ff54042b4db371a3417f322
Source dataset
uspto-grants-2012_04
Patent number
US08148401B2

Reaction notes

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