4-Methylmorpholine → HCID 24743388, compound

HRID 252456Notes

Reaction equation

HRID 252456 reaction equation
[NH2:1][C:2]1[C:11]([C@H:12]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:13][CH2:14][C:15](O)=[O:16])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:8]=2)[N:3]=1.ClC(OCC(C)C)=O.CN1CCOCC1.[CH3:46][C:47]([CH3:59])([CH3:58])[CH2:48][CH2:49][NH:50][CH2:51][C:52]1[N:53]([CH3:57])[CH:54]=[CH:55][N:56]=1>ClCCl.C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:11]([C@H:12]([CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:13][CH2:14][C:15]([N:50]([CH2:49][CH2:48][C:47]([CH3:59])([CH3:58])[CH3:46])[CH2:51][C:52]2[N:53]([CH3:57])[CH:54]=[CH:55][N:56]=2)=[O:16])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:8]=2)[N:3]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 57475711HCID 57475711, compoundHCID 67268164HCID 67268164, compound

Product 1

HCID 24743388HCID 24743388, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

To an ice cold solution of 4-(2-amino-6-phenoxy-quinoline-3-yl)-4-(S)-cyclohexyl-butyric acid (0.085 mg, 0.19 mmol) in dichloromethane (2.0 mL) was added isobutyl chloroformate (0.025 mL, 0.19 mmol) and N-methylmorpholine (0.021 mL, 0.019 mmol). The reaction mixture was stirred at this temperature for 0.5 h. The reaction mixture was then reacted with a solution of (3,3-dimethyl-butyl)-(1-methyl-1H-imidazole-2-ylmethyl)-amine (0.037 mg, 0.19 mmol) in dichloromethane (0.5 mL) and stirred at 0° C. for 0.5 h. To this reaction mixture was added CHCl3, and the resulting mixture was washed with H2O and saturated aqueous NaHCO3 solution. The organic layer was dried (MgSO4) and concentrated in vacuo to yield crude material. The crude material was purified by silica gel column chromatography using 4% MeOH in CHCl3 to yield 4-(2-amino-6-phenoxy-quinolin-3-yl)-4-(S)-cyclohexyl-N-(3,3-dimethyl-butyl)-N-(1-methyl-1H-imidazol-2-ylmethyl)-butyramide as a solid.

Workup

  1. stirringstirred at 0° C. for 0.5 h
  2. washthe resulting mixture was washed with H2O and saturated aqueous NaHCO3 solution
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto yield crude material
  6. customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d790e203031348b1b90b52fc1e0ef760
Source dataset
uspto-grants-2011_01
Patent number
US07868022B2

Reaction notes

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