Acetic Acid → HCID 44155146, compound

HRID 910480Notes

Reaction equation

HRID 910480 reaction equation
[CH3:1][N:2](C)/[CH:3]=[N:4]/[NH:5][C:6](=O)[CH2:7][C@H:8]1[CH2:13][C@H:12]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][O:21][CH2:22][C@H:23]([O:25][CH2:26][CH3:27])[CH3:24])=[CH:16][CH:15]=2)[C@@H:11]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][C:33]3[O:38][CH2:37][CH2:36][N:35]([CH2:39][CH2:40][CH2:41][O:42][CH3:43])[C:34]=3[CH:44]=2)[CH2:10][N:9]1S(C1C=CC(C)=CC=1)(=O)=O.CN.C(O)(=O)C.C([O-])(O)=O.[Na+]>C(#N)C>[CH2:26]([O:25][C@H:23]([CH3:24])[CH2:22][O:21][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([C@H:12]2[CH2:13][C@H:8]([CH2:7][C:6]3[N:2]([CH3:1])[CH:3]=[N:4][N:5]=3)[NH:9][CH2:10][C@@H:11]2[O:28][CH2:29][C:30]2[CH:31]=[CH:32][C:33]3[O:38][CH2:37][CH2:36][N:35]([CH2:39][CH2:40][CH2:41][O:42][CH3:43])[C:34]=3[CH:44]=2)=[CH:15][CH:16]=1)[CH3:27]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 516892Sodium BicarbonateHCID 87381617HCID 87381617, compound

Product 1

HCID 44155146HCID 44155146, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

Into a solution of 1.0 mmol of [(2R,4R,5R)-4-[4-((R)-2-ethoxy-propoxymethyl)-phenyl]-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl) -piperidin-2-yl]-acetic acid [1-dimethylamino-meth-(E)-ylidene]- hydrazide in 2 ml of acetonitrile is condensed ca. 1 ml of gaseous methylamine, at RT. Acetic acid (2 mL) is carefully added, then the reaction system is sealed, and heated at 100° C. for 4 h. The reaction mixture is cooled to RT, poured into saturated aqueous NaHCO3, and extracted with EtOAc (3×). The combined organic extracts are dried over Na2SO4, concentrated under reduced pressure, and purified by flash chromatography (SiO2 60 F), to afford the title compound, which is identified based on its Rf value.

Workup

  1. customat RT
  2. customthe reaction system is sealed
  3. temperatureThe reaction mixture is cooled to RT
  4. extractionextracted with EtOAc (3×)
  5. dry with materialThe combined organic extracts are dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. custompurified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-3f1b876a9be54647bab88ff5934460df
Source dataset
uspto-grants-2011_09
Patent number
US08022069B2

Reaction notes

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