Isopropanol hydrochloride → HCID 86655871, compound

HRID 2047494Notes

Reaction equation

HRID 2047494 reaction equation
[F:1][C:2]([F:50])([F:49])[C:3]1[CH:4]=[C:5]([N:13]([CH3:48])[C:14]([N:16]([CH3:47])[C@H:17]2[C@H:21]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH2:20][N:19]([C:29]3[O:33][C:32]([CH:34]4[CH2:39][CH2:38][N:37]([C:40](OC(C)(C)C)=[O:41])[CH2:36][CH2:35]4)=[N:31][N:30]=3)[CH2:18]2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Cl.[CH3:52]C(O)C>>[C:40]([N:37]1[CH2:38][CH2:39][CH:34]([C:32]2[O:33][C:29]([N:19]3[CH2:20][C@@H:21]([C:22]4[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=4)[C@H:17]([N:16]([CH3:47])[C:14]([N:13]([C:5]4[CH:4]=[C:3]([C:2]([F:49])([F:1])[F:50])[CH:8]=[C:7]([C:9]([F:10])([F:12])[F:11])[CH:6]=4)[CH3:48])=[O:15])[CH2:18]3)=[N:30][N:31]=2)[CH2:35][CH2:36]1)(=[O:41])[CH3:52]

Participants

3

Reactant 2

HCID 21912024Isopropanol hydrochlorideHCID 86655872HCID 86655872, compound

Product 1

HCID 86655871HCID 86655871, compoundYield 43%

Procedure

A mixture of the compound (0.10 g) obtained in step 1 and 2N hydrogen chloride/2-propanol was stirred at room temperature for 3 days. The mixture was concentrated under reduced pressure, and to the residue were added acetyl chloride (0.016 mL), triethylamine (0.071 mL) and acetonitrile (4.0 mL), and the mixture was stirred at room temperature for 3 hr. The mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH Chromatorex) (solvent gradient; 50→100% ethyl acetate/hexane) to give the title compound (0.041 g, 43%) as a pale-brown powder.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionto the residue were added acetyl chloride (0.016 mL), triethylamine (0.071 mL) and acetonitrile (4.0 mL)
  3. stirringthe mixture was stirred at room temperature for 3 hr
  4. additionThe mixture was diluted with ethyl acetate
  5. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (NH Chromatorex) (solvent gradient; 50→100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3d267f0164324b57a940a95f05b2fcf3
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

Loading…