Diisopropylethylamine → HCID 66972804, compound

HRID 1367814Notes

Reaction equation

HRID 1367814 reaction equation
[CH:1]1([CH2:4][S:5]([CH2:8][C@H:9]([NH:13][C@@H:14]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:15]([F:17])[F:16])[C:10]([OH:12])=O)(=[O:7])=[O:6])[CH2:3][CH2:2]1.Cl.[NH2:26][C:27]1([C:30]#[N:31])[CH2:29][CH2:28]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:30]([C:27]1([NH:26][C:10](=[O:12])[CH:9]([NH:13][CH:14]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:15]([F:17])[F:16])[CH2:8][S:5]([CH2:4][CH:1]2[CH2:2][CH2:3]2)(=[O:7])=[O:6])[CH2:29][CH2:28]1)#[N:31]

Participants

6

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 145863631-Amino-1-cyclopropanecarbonitrile hydrochlorideHCID 66972587HCID 66972587, compound

Product 1

HCID 66972804HCID 66972804, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-cyclopropylmethylsulfonyl-2(R)-[2,2,-difluoro-1(S)-(4-fluorophenyl)-ethylamino]propionic acid (0.95 g), 1-aminocyclopropanecarbonitrile HCl salt (400 mg) in DMF (5 mL) at room temperature was added HATU (1.28 g), followed by diisopropylethylamine (1.68 g/2.26 mL). After being stirred at room temperature for 4 hours, the reaction mixture was concentrated under reduced pressure and then partitioned between ethyl acetate and brine. The combined organic extracts were dried over anhydrous MgSO4 and concentrated under reduced pressure, and the residue was purified by recrystallization from 2-propanol to yield N-(1-cyano-cyclopropyl)-3-cyclopropylmethanesulfonyl-2-[2,2-difluoro-1-(4-fluorophenyl)ethylamino]-propionamide as colorless crystals (250 mg).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. custompartitioned between ethyl acetate and brine
  3. dry with materialThe combined organic extracts were dried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was purified by recrystallization from 2-propanol

Sources & evidence

ORD record
ord-9c7c46a41858474ea8e384e13720ab33
Source dataset
uspto-grants-2011_02
Patent number
US07893093B2

Reaction notes

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