Morpholine → HCID 57886896, compound

HRID 1819307Notes

Reaction equation

HRID 1819307 reaction equation
ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.[C:29]([O:33][C:34]([NH:36][C@@H:37]1[CH2:42][CH2:41][CH2:40][N:39]([C:43]2[N:51]([CH2:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=3[Cl:59])[C:50]3[C:49](=[O:60])[N:48]([CH3:61])[C:47](=[O:62])[N:46]([CH3:63])[C:45]=3[C:44]=2[C:64](O)=[O:65])[CH2:38]1)=[O:35])([CH3:32])([CH3:31])[CH3:30].[Cl-].[NH4+]>CN(C)C=O.C(N(CC)CC)C>[Cl:59][C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][C:53]=1[CH2:52][N:51]1[C:50]2[C:49](=[O:60])[N:48]([CH3:61])[C:47](=[O:62])[N:46]([CH3:63])[C:45]=2[C:44]([C:64]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[O:65])=[C:43]1[N:39]1[CH2:40][CH2:41][CH2:42][C@@H:37]([NH:36][C:34](=[O:35])[O:33][C:29]([CH3:30])([CH3:31])[CH3:32])[CH2:38]1

Participants

8

Reactant 5

HCID 8083MorpholineHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57886968HCID 57886968, compound

Product 1

HCID 57886896HCID 57886896, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

1-Hydroxybenzotriazole (117 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (147 mg), triethylamine (0.21 ml) and morpholine (63 μl) were added to a solution of 6-{(3R)-3-[(tertbutoxycarbonyl)amino]piperidin-1-yl}-5-(2-chlorobenzyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (140 mg) in N,N-dimethylformamide (3 ml), and the resulting mixture was stirred at 25° C. for 20 hours. A saturated aqueous ammonium chloride solution was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by a preparative thin-layer chromatography (hexane/ethyl acetate=2/1) to obtain the title compound (106 mg) as a white solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by a preparative thin-layer chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-7fc701b982f94a759507e74f81061cac
Source dataset
uspto-grants-2009_10
Patent number
US07601728B2

Reaction notes

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