4-Methylmorpholine → HCID 66972513, compound

HRID 1367811Notes

Reaction equation

HRID 1367811 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 layers were dried with MgSO4 and the solvent was removed under the reduced pressure to give N-(1-cyanocyclopropyl)-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 layers were dried with MgSO4
  5. customthe solvent was removed under the reduced pressure

Sources & evidence

ORD record
ord-9a4c76b886cd47628be8f2bf52bd718b
Source dataset
uspto-grants-2011_02
Patent number
US07893093B2

Reaction notes

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