Hydrochloric Acid → HCID 60139888, compound

HRID 468079Notes

Reaction equation

HRID 468079 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][C:7]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:11]([C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])[N:10]=[C:9]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[F:24])[O:8]1.CCN(C(C)C)C(C)C.[C:40](Cl)(=[O:44])[CH:41]([CH3:43])[CH3:42].Cl>C(Cl)Cl>[F:24][C:18]1[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:17]=1[C:9]1[O:8][C:7]([CH2:6][CH2:5][CH2:4][NH:3][C:40](=[O:44])[CH:41]([CH3:43])[CH3:42])([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:11]([C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])[N:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 62325Isobutyryl chlorideHCID 81531DiisopropylethylamineHCID 67215229HCID 67215229, compound

Product 1

HCID 60139888HCID 60139888, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-oxadiazol-3(2H)-yl)-2-methylpropan-1-one dihydrochloride, prepared as in the above examples, (50 mg, 0.11 mmol) in anhydrous CH2Cl2 (1 mL) was added DIEA (95 μL, 0.54 mmol) followed by isobutyryl chloride (17 μL, 0.16 mmol). After stirring at room temperature for 16 hours the mixture was treated with 1N HCl (10 mL) and extracted with CH2Cl2 (2×10 mL). The combined organic phases were washed with brine (10 mL) then dried over Na2SO4 and concentrated. The residue was chromatographed (4:1 to 2:1 hexanes/EtOAc) to afford the product (31 mg, 62%) as a colorless gum. MS ESI (+) m/z 458.1 (M+1) detected; 1H NMR (400 MHz, CDCl3) δ 7.55 (m, 3H), 7.36 (m, 3H), 7.17 (m, 2H), 3.33 (m, 3H), 3.04 (m, 1H), 2.53 (m, 1H), 2.35 (m, 1H), 1.77 (m, 1H), 1.56 (m, 1H), 1.16 (m, 12H).

Workup

  1. extractionextracted with CH2Cl2 (2×10 mL)
  2. washThe combined organic phases were washed with brine (10 mL)
  3. dry with materialthen dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed (4:1 to 2:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-fc87df6a92fa4cbe9fe67185dabde5e8
Source dataset
uspto-grants-2014_01
Patent number
US08623895B2

Reaction notes

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