4-Methylmorpholine → HCID 67507348, compound

HRID 1829132Notes

Reaction equation

HRID 1829132 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[C:24]([Cl:25])=[CH:23][C:22]([C:26]([OH:28])=O)=[CH:21][N:20]=3)[CH2:15][CH2:14]2)[CH2:10][C@H:9]1[C:29]([N:31]1[CH2:35][CH2:34][S:33][CH2:32]1)=[O:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.Cl.C(C1C=C(Cl)C(N2CCN([C@@H]3CN[C@H](C(N4CCSC4)=O)C3)CC2)=[N:46]C=1)(O)=O.[Cl-].[NH4+].CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[C:24]([Cl:25])=[CH:23][C:22]([C:26](=[O:28])[NH2:46])=[CH:21][N:20]=3)[CH2:15][CH2:14]2)[CH2:10][C@H:9]1[C:29]([N:31]1[CH2:35][CH2:34][S:33][CH2:32]1)=[O:30])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 6

HCID 79724-MethylmorpholineHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67506869HCID 67506869, compoundHCID 67506888HCID 67506888, compound

Product 1

HCID 67507348HCID 67507348, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-{(2S,4S)-1-tert-Butoxycarbonyl-4-[4-(5-carboxy-3-chloro-2-pyridyl)-1-piperazinyl]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine [product of Example 217 (1), 2.63 g] and ammonium chloride (0.54 g) were dissolved in DMF (30 mL), and N-methylmorpholine (1.1 mL), HOBT (1.53 g) and EDC hydrochloride (1.15 g) were successively added thereto. The mixture was stirred at room temperaturte for 4 hr. The reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium hydrogencarbonate solution was added to the residue. The mixture was extracted with ethyl acetate. The extract washed with brine and dried. The solvent was evaporated under reduced pressure to give 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[4-(5-carbamoyl-3-chloro-2-pyridyl)-1-piperazinyl]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine (2.50 g) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium hydrogencarbonate solution
  2. additionwas added to the residue
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe extract washed with brine
  5. customdried
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c7d0560cc9564e3e86e3d85eca8451d9
Source dataset
uspto-grants-2006_06
Patent number
US07060722B2

Reaction notes

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