4-Methylmorpholine → HCID 66972513, compound

HRID 1696063Notes

Reaction equation

HRID 1696063 reaction equation
[F:1][C:2]([F:26])([F:25])[C@@H:3]([NH:11][C@@H:12]([CH2:16][S:17][CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[C:13]([OH:15])=O)[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1.[NH2:27][C:28]1([C:31]#[N:32])[CH2:30][CH2:29]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.[NH4+].[Cl-]>CN(C=O)C.C(OCC)(=O)C>[C:31]([C:28]1([NH:27][C:13](=[O:15])[C@@H:12]([NH:11][C@@H:3]([C:4]2[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=2)[C:2]([F:1])([F:26])[F:25])[CH2:16][S:17][CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH2:30][CH2:29]1)#[N:32]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 25517Ammonium ChlorideHCID 5568881-AminocyclopropanecarbonitrileHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66972538HCID 66972538, compound

Product 1

HCID 66972513HCID 66972513, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2(R)-[2,2,2-trifluoro-1(S)-(4-fluorophenyl)ethylamino]-3-(pyridin-3-ylmethylsulfanyl)-propionic acid was dissolved in DMF (5 ml) and 1-aminocyclopropanecarbonitrile (142 mg, 1.2 mmol), HATU (456 mg, 1.2 mmol) and NMM (0.44 ml, 4 mmol) were added. After stirring for 2 h at rt, saturated NH4Cl and ethyl acetate were added and stirring was continued for 20 min. The aqueous layer was extracted with ethyl acetate. The combined organic layer was dried with MgSO4 and the solvent was removed under reduced pressure to give N-(1-cyano-cyclopropyl)-2(R)-[2,2,2-trifluoro-1(S)-(4-fluorophenyl)ethylamino]-3-(pyridin-3-ylmethylsulfanyl)propionamide as an oil. The crude was used in the next step without further purification.

Workup

  1. stirringstirring
  2. waitwas continued for 20 min
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe combined organic layer was dried with MgSO4
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-bff5a658ab1b479a8d2a32e92befff34
Source dataset
uspto-grants-2012_04
Patent number
US08163735B2

Reaction notes

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