HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Pyridine → HCID 68549880, compound

HRID 2388568
Notes
Print preview

Reaction equation

HRID 2388568 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([NH:11][C@@H:12]([C:16]2[O:17][C:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=3)=[N:19][N:20]=2)[C@@H:13]([OH:15])[CH3:14])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].N1C=CC=CC=1.[C:35](Cl)(=[O:38])[CH2:36][CH3:37]>C(Cl)Cl>[C:35]([O:15][C@@H:13]([CH3:14])[C@@H:12]([NH:11][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([Cl:1])[C:9]=1[CH3:10])[C:16]1[O:17][C:18]([C:21]2[CH:22]=[CH:23][C:24]([C:27]#[N:28])=[CH:25][CH:26]=2)=[N:19][N:20]=1)(=[O:38])[CH2:36][CH3:37]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 442008822-Chloro-4-(((1R,2S)-1-(5-(4-cyanophenyl)-1,3,4-oxadiazol-2-yl)-2-hydroxypropyl)amino)-3-methylbenzonitrile

Product 1

HCID 68549880HCID 68549880, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

To a 50 mL round bottomed flask was added 2-chloro-4-((1R,2S)-1-(5-(4-cyanophenyl)-1,3,4-oxadiazol-2-yl)-2-hydroxypropylamino)-3-methylbenzonitrile (200 mg, 0.508 mmol, pyridine (1 mL, 12.41 mmol) and methylene chloride (15 mL). Propionyl chloride (0.22 mL, 2.54 mmol) was then added dropwise and the mixture was stirred at room temperature for 19 h. The reaction mixture was then quenched with 10% aq HCl (15 mL) and methylene chloride (30 mL) was added. The phases were partitioned and the aqueous phase extracted with methylene chloride (30 mL) (×2). The combined organics were washed with a saturated solution of sodium hydrogen carbonate, dried (Na2SO4) and concentrated to furnish a yellow oil (0.116 g, 52%). 1H NMR (Acetone d6, 400 MHz) δ 8.23 (d, J=9 Hz, 2H), 8.00 (d, J=9 Hz, 2H), 7.53 (d, J=9 Hz, 1H), 7.02 (d, J=9 Hz, 1H), 5.73 (d, J=9 Hz, 1H), 5.69-5.64 (m, 1H), 5.48 (dd, J=5 and 8 Hz, 1H), 2.37 (s, 3H), 2.34 (q, J=7 Hz, 1H), 1.47 (d, J=6 Hz, 3H) and 1.02 (t, J=8 Hz, 3H).

Workup

  1. customThe reaction mixture was then quenched with 10% aq HCl (15 mL) and methylene chloride (30 mL)
  2. additionwas added
  3. customThe phases were partitioned
  4. extractionthe aqueous phase extracted with methylene chloride (30 mL) (×2)
  5. washThe combined organics were washed with a saturated solution of sodium hydrogen carbonate
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1ef074ccd02a45edb574d00b62510dbf
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08268872B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes