Hydrochloric Acid → HCID 67224497, compound

HRID 1848934Notes

Reaction equation

HRID 1848934 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:18]=[C:17]([N:19]3[CH2:24][CH2:23][N:22]([CH2:25][C:26]4[CH2:27][C:28]5([CH2:34][CH2:35][C:36]=4[C:37]4[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=4)[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]5)[CH2:21][CH2:20]3)[CH:16]=[CH:15][C:10]=2[C:11]([O:13]C)=[O:12])=[CH:4][C:3]=1[Cl:44].[F:45][CH2:46][C:47](=O)[CH2:48][F:49].C(O[BH3-])(=O)C.[Na+].O[Li].O.Cl>ClCCl.C(OCC)(=O)C.O1CCCC1.O.CO>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:18]=[C:17]([N:19]3[CH2:24][CH2:23][N:22]([CH2:25][C:26]4[CH2:27][C:28]5([CH2:34][CH2:35][C:36]=4[C:37]4[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=4)[CH2:33][CH2:32][N:31]([CH:47]([CH2:48][F:49])[CH2:46][F:45])[CH2:30][CH2:29]5)[CH2:21][CH2:20]3)[CH:16]=[CH:15][C:10]=2[C:11]([OH:13])=[O:12])=[CH:4][C:3]=1[Cl:44]

Participants

11

Reactant 5

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 2283971,3-DifluoroacetoneHCID 23670382SodiumacetoxyborohydrideHCID 67226815HCID 67226815, compound

Product 1

HCID 67224497HCID 67224497, compound

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of EXAMPLE 391H (318 mg) in dichloromethane (4 mL) was added 1,3-difluoropropan-2-one (282 mg) and sodium acetoxyborohydride (318 mg). The mixture was stirred overnight. The reaction mixture was diluted with ethyl acetate (300 mL) and washed with 2N aqueous NaOH and brine, and dried over Na2SO4. Filtration and concentration gave the crude product which was dissolved in tetrahydrofuran (10 mL), methanol (5 mL) and water (5 mL). LiOH.H2O (450 mg) was added and the mixture was stirred overnight. The mixture was neutralized with 2N aqueous HCl and extracted with ethyl acetate (300 mL) and dichloromethane (300 mL) respectively. The organic extracts were combined and dried over Na2SO4. Filtration and concentration provided the title compound.

Workup

  1. washwashed with 2N aqueous NaOH and brine
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration and concentration
  4. customgave the crude product which
  5. stirringthe mixture was stirred overnight
  6. extractionextracted with ethyl acetate (300 mL) and dichloromethane (300 mL) respectively
  7. dry with materialdried over Na2SO4
  8. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-8459eecea9704c8898dbce3550fe5043
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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