4-Methylmorpholine → HCID 58999573, compound

HRID 1593601Notes

Reaction equation

HRID 1593601 reaction equation
[CH2:1]([N:8]1[CH2:17][C:16]2[N:15]=[CH:14][CH:13]=[C:12]([NH2:18])[C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.[C:26]12([CH2:36][C:37](Cl)=[O:38])[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[CH2:27]1)[CH2:33]2>O1CCOCC1>[C:26]12([CH2:36][C:37]([NH:18][C:12]3[C:11]4[CH2:10][CH2:9][N:8]([CH2:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)[CH2:17][C:16]=4[N:15]=[CH:14][CH:13]=3)=[O:38])[CH2:33][CH:32]3[CH2:31][CH:30]([CH2:29][CH:28]([CH2:34]3)[CH2:27]1)[CH2:35]2

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 27718821-Adamantaneacetyl chlorideHCID 58999575HCID 58999575, compound

Product 1

HCID 58999573HCID 58999573, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

7-Benzyl-5,6,7,8-tetrahydro-[1,7]naphthyridin-4-ylamine (48 mg, 0.202 mmol) in 6 ml of dioxane was treated with NMM (22 μl, 0.202 mmol) followed by adamantan-1-yl-acetyl chloride (0.043 g, 0.202 mmol) and stirred at rt under argon. The reaction was monitored by TLC and LCMS. Excess acid chloride was added and the reaction was stirred. The contents were concentrated and purified by HPLC to afford the desired product (3.3 mg, 4%).

Workup

  1. stirringthe reaction was stirred
  2. concentrationThe contents were concentrated
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-33807ac6f3c2442ba4008503042a07ad
Source dataset
uspto-grants-2007_11
Patent number
US07297700B2

Reaction notes

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