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

Diisopropylethylamine → HCID 67469768, compound

HRID 408005
Notes
Print preview

Reaction equation

HRID 408005 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][C@H:14]1[CH2:18][CH2:17][N:16]([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[C:15]1=[O:25])[C:6]([O:8][CH3:9])=[O:7].C(N(C(C)C)C(C)C)C.[Cl:35][C:36]1[CH:37]=[C:38]([F:43])[C:39](F)=[N:40][CH:41]=1>CN(C=O)C.CCOC(C)=O>[Cl:35][C:36]1[CH:37]=[C:38]([F:43])[C:39]([N:22]2[CH2:23][CH2:24][CH:19]([N:16]3[CH2:17][CH2:18][C@H:14]([O:13][C:12]4[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=4[F:2])[C:15]3=[O:25])[CH2:20][CH2:21]2)=[N:40][CH:41]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27832485-Chloro-2,3-difluoropyridineHCID 67469793(S)-methyl 3-fluoro-4-(2-oxo-1-(piperidin-4-yl)pyrrolidin-3-yloxy)benzoate hydrochloride

Product 1

HCID 67469768HCID 67469768, compoundYield 54.6%

Reagents, catalysts & solvents 2

HCID 6228Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (S)-methyl 3-fluoro-4-(2-oxo-1-(piperidin-4-yl)pyrrolidin-3-yloxy)benzoate hydrochloride (Example 151, Step B; 2.0 g, 5.9 mmol) in DMF (3 mL) was added N-ethyl-N-isopropylpropan-2-amine (3.8 g, 30 mmol) and 5-chloro-2,3-difluoropyridine (2.7 g, 18 mmol) and the reaction was heated to 60° C. overnight. The reaction was next diluted with EtOAc (30 mL) and washed with water (30 mL), and brine (30 mL), and the combined organic phases were dried over MgSO4, filtered and concentrated under vacuum. The crude material was purified on silica using a gradient of DCM to 1:19 EtOAc:DCM as eluent to yield (S)-methyl 4-(1-(1-(5-chloro-3-fluoropyridin-2-yl)piperidin-4-yl)-2-oxopyrrolidin-3-yloxy)-3-fluorobenzoate (1.5 g, 54%)

Workup

  1. washwashed with water (30 mL), and brine (30 mL)
  2. dry with materialthe combined organic phases were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe crude material was purified on silica using a gradient of DCM to 1:19 EtOAc

Sources & evidence

ORD record
ord-afc7fc35376a40339af74e232a43d22f
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08754226B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes