Acetic Acid → HCID 68751986, compound

HRID 1864800Notes

Reaction equation

HRID 1864800 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[O:15]=[C:16]1[N:20]([C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19]2[CH:40]=[CH:41][C:42]([C:44]3[CH:45]=[C:46]([CH:49]=O)[O:47][CH:48]=3)=[CH:43][C:18]=2[O:17]1.[CH3:51][N:52]1[CH2:57][CH2:56][CH:55]([NH2:58])[CH2:54][CH2:53]1.C(O)(=O)C>ClCCCl.ClCCl>[CH3:51][N:52]1[CH2:57][CH2:56][CH:55]([NH:58][CH2:49][C:46]2[O:47][CH:48]=[C:44]([C:42]3[CH:41]=[CH:40][C:19]4[N:20]([C:21]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=5)[C:16](=[O:15])[O:17][C:18]=4[CH:43]=3)[CH:45]=2)[CH2:54][CH2:53]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 27375314-Amino-1-methylpiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 86616470HCID 86616470, compound

Product 1

HCID 68751986HCID 68751986, compoundYield 41.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (339 mg, 1.6 mmol) was added to a solution of 4-(2-oxo-3-trityl-2,3-dihydro-benzooxazol-6-yl)-furan-2-carbaldehyde (377 mg, 0.8 mmol) and 1-methyl-piperidin-4-ylamine (219 mg, 1.92 mmol) and acetic acid (192 mg, 3.2 mmol) in 10 mL of 1,2-dichloroethane. The mixture was stirred at ambient temperature for 21 h, and then it was diluted with dichloromethane and washed with saturated sodium carbonate solution. The aqueous phase was extracted with dichloromethane, and the combined organic phases were washed with water and brine, dried over magnesium sulfate, filtered and concentrated to leave the crude product. Chromatography (elution with dichloromethane/methanol/acetic acid/water) gave 189 mg of product. LC/MS: Retention time, 2.38 min; (M+H)=570.

Workup

  1. washwashed with saturated sodium carbonate solution
  2. extractionThe aqueous phase was extracted with dichloromethane
  3. washthe combined organic phases were washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto leave the crude product
  8. washChromatography (elution with dichloromethane/methanol/acetic acid/water)

Sources & evidence

ORD record
ord-a20d3b78a22642729dad7936a7902df0
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

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