Morpholine → HCID 23510158, compound

HRID 1883131Notes

Reaction equation

HRID 1883131 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[C:13]([CH:15]([NH:20][C:21]([CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[NH:29][C:30]([C:32]1[N:33]([CH2:42][CH2:43][CH2:44]Cl)[C:34]2[C:39]([CH:40]=1)=[CH:38][CH:37]=[C:36]([Cl:41])[CH:35]=2)=[O:31])=[O:22])[CH2:16][CH:17]([CH3:19])[CH3:18])#[N:14]>CN(C=O)C>[C:13]([CH:15]([NH:20][C:21]([CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[NH:29][C:30]([C:32]1[N:33]([CH2:42][CH2:43][CH2:44][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[C:34]2[C:39]([CH:40]=1)=[CH:38][CH:37]=[C:36]([Cl:41])[CH:35]=2)=[O:31])=[O:22])[CH2:16][CH:17]([CH3:19])[CH3:18])#[N:14]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 20740305HCID 20740305, compound

Product 1

HCID 23510158HCID 23510158, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred slurry of morpholine (0.05 ml, 0.51 mmol) and potassium carbonate (0.09 g, 0.68 mmol) in DMF (1.2 ml) was added 6-Chloro-1-(3-chloro-propyl)-1H-indole-2-carboxylic acid [2-(1-cyano-3-methyl-butylcarbamoyl)-cyclohexyl]-amide from Example 19 (0.17 g, 0.34 mmol) at room temperature. The reaction was stirred for 48 hours before being partitioned between ethyl acetate and 1N NaOH. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The resulting crude oil was chromatographed (5% MeOH/dichloromethane) to yield 6-chloro-1-(3-morpholin-4-yl-propyl)-1H-indole-2-carboxylic acid [2-(1-cyano-3-methyl-butylcarbamoyl)-cyclohexyl]-amide (0.05 g, 27%); [M+H=543].

Workup

  1. custombefore being partitioned between ethyl acetate and 1N NaOH
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting crude oil was chromatographed (5% MeOH/dichloromethane)

Sources & evidence

ORD record
ord-9e052252143a4b2bb4feda254415b43d
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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