Morpholine → HCID 53851224, compound

HRID 1956516Notes

Reaction equation

HRID 1956516 reaction equation
Cl.[CH2:2]([O:9][C:10]([N:12]([CH2:35][CH2:36][CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=1)[CH2:13][CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:24]([OH:26])=O)[CH:22]=2)[NH:17][C:16]=1[C:27]1[CH:32]=[C:31]([CH3:33])[CH:30]=[C:29]([CH3:34])[CH:28]=1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH:78]1[CH2:83][CH2:82][O:81][CH2:80][CH2:79]1>C(Cl)Cl>[CH2:2]([O:9][C:10](=[O:11])[N:12]([CH2:13][CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:24]([N:78]3[CH2:83][CH2:82][O:81][CH2:80][CH2:79]3)=[O:26])[CH:22]=2)[NH:17][C:16]=1[C:27]1[CH:32]=[C:31]([CH3:33])[CH:30]=[C:29]([CH3:34])[CH:28]=1)[CH2:35][CH2:36][CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 2724699PyBOPHCID 69950775HCID 69950775, compound

Product 1

HCID 53851224HCID 53851224, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 100 mg (0.163 mnmol) of 3-[2-[benzyloxycarbonyl-[4-(pyridin-4-yl)butyl]amino]ethyl]-2-(3,5 -dimethylphenyl)-1H-indole-5-carboxylic acid hydrochloride 101.7 mg (0.196 mmol) of PyBOP reagent, 0.085 mL (85.2 mg, 0.978 mmol) of morpholine, and 1 mL of dry methylene chloride was stirred under nitrogen at room temperature in a stoppered flask. After 5 days, the solution was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic phase was dried over sodium sulfate, filtered, and concentrated in vacuo. Purification of the crude product by flash chromatography on silica gel (gradient elution with 1-4% MeOH in CH2 Cl2) afforded a quantitative yield of the title compound as a yellow gum; homogeneous by TLC in 95:5 CH2Cl2 --MeOH. 500 MHz 1H NMR (CDCl3) was complex, owing to rotamners, but was consistent with the assigned structure. Mass spectrum (ESI): m/e=645.6 (M+H).

Workup

  1. customthe solution was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification of the crude product by flash chromatography on silica gel (gradient elution with 1-4% MeOH in CH2 Cl2)

Sources & evidence

ORD record
ord-8435feb5c3f642119394430f026d83c4
Source dataset
uspto-grants-1998_07
Patent number
US05780437

Reaction notes

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