4-Methylmorpholine → HCID 178496576, compound

HRID 416022Notes

Reaction equation

HRID 416022 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:24]2[CH:29]=[CH:28][C:27]([C:30](O)=[O:31])=[CH:26][CH:25]=2)[CH:5]=[C:6]([Cl:23])[C:7]=1[CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C@H:14]2[CH2:19][CH2:18][C@H:17]([O:20][CH3:21])[CH2:16][CH2:15]2)[C:10]1=[O:22].Cl.CN(C)CCCN=C=NCC.CN1CCOCC1.OC1C2N=NNC=2C=CC=1.Cl.[F:63][C:64]([F:72])([F:71])[CH:65]1[CH2:70][CH2:69][NH:68][CH2:67][CH2:66]1>C(Cl)Cl>[Cl:23][C:6]1[CH:5]=[C:4]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([N:68]3[CH2:69][CH2:70][CH:65]([C:64]([F:72])([F:71])[F:63])[CH2:66][CH2:67]3)=[O:31])=[CH:26][CH:25]=2)[CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C@H:14]2[CH2:19][CH2:18][C@H:17]([O:20][CH3:21])[CH2:16][CH2:15]2)[C:10]1=[O:22]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 162181604-(Trifluoromethyl)piperidine hydrochlorideHCID 178418300HCID 178418300, compoundHCID 178496577HCID 178496577, compound

Product 1

HCID 178496576HCID 178496576, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Mix 3′,5′-dichloro-4′-[(R)-trans-1-(4-methoxy-cyclohexyl)-2-oxo-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic acid (0.350 g, 0.74 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.216 g, 1.11 mmol), N-methylmorpholine (0.33 mL, 2.95 mmol), hydroxybenzotriazole (0.247 g, 0.74 mmol) and 4-trifluoromethyl-piperidine hydrochloride (0.226 g, 1.47 mmol) in CH2Cl2 (10 mL). Stir for 12 hours at room temperature. Quench with 1N HCl and extract with ethyl acetate. Wash the extract with saturated aqueous sodium bicarbonate brine. Dry over magnesium sulfate, filter, and concentrate under vacuum. Purify by flash column chromatography to recover 0.350 g (78%) of the title compound: MS (m/z): 611 (M+).

Workup

  1. customQuench with 1N HCl
  2. extractionextract with ethyl acetate
  3. washWash the
  4. extractionextract with saturated aqueous sodium bicarbonate brine
  5. dry with materialDry over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under vacuum
  8. customPurify by flash column chromatography
  9. customto recover 0.350 g (78%) of the title compound

Sources & evidence

ORD record
ord-924441bdd62249709b0c5798558fec16
Source dataset
uspto-grants-2012_01
Patent number
US08088776B2

Reaction notes

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