Diisopropylethylamine → HCID 59249548, compound

HRID 1807125Notes

Reaction equation

HRID 1807125 reaction equation
[Cl:1][C:2]1[C:3]([F:31])=[C:4]([CH:8]2[C:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[CH:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[NH:10][CH:9]2[C:28]([OH:30])=O)[CH:5]=[CH:6][CH:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH:65]1[CH2:70][CH2:69][CH:68]([CH2:71][C:72]([NH2:74])=[O:73])[CH2:67][CH2:66]1>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[C:3]([F:31])=[C:4]([C@@H:8]2[C@:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:25])([CH3:26])[CH3:27])[NH:10][C@H:9]2[C:28]([N:65]2[CH2:70][CH2:69][CH:68]([CH2:71][C:72]([NH2:74])=[O:73])[CH2:67][CH2:66]2)=[O:30])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 220649342-(Piperidin-4-yl)acetamideHCID 666882513-(3-Chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid

Product 1

HCID 59249548HCID 59249548, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of rac (2R,3S,4R,5S)-3-(3-Chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid (80 mg, 0.138 mmol) in methylene chloride (10 mL), HATU (Aldrich, 79 mg, 0.21 mmol) was added followed by the addition of DIPEA (0.145 mL, 0.83 mmol) and piperidin-4-yl-acetamide (Chembridge, 41 mg, 0.21 mmol). The mixture was stirred at rt for 3 hrs then overnight after the addition of 3 mL of DMF. The reaction was quenched with addition of water. The mixture was extracted with methylene chloride (2×10 mL) and the extracts were dried with magnesium sulfate. The solvent was removed and the residue was purified on an ISCO machine (12 g column, eluent, 20% EtOAc/methylene chloride) to give a white solid. 21 mg.

Workup

  1. customThe reaction was quenched with addition of water
  2. extractionThe mixture was extracted with methylene chloride (2×10 mL)
  3. dry with materialthe extracts were dried with magnesium sulfate
  4. customThe solvent was removed
  5. customthe residue was purified on an ISCO machine (12 g column, eluent, 20% EtOAc/methylene chloride)
  6. customto give a white solid

Sources & evidence

ORD record
ord-8fb7a97d73d7469fba56dd70b79df7e6
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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