Pyridine → HCID 117667658, compound

HRID 712763Notes

Reaction equation

HRID 712763 reaction equation
[N:1]1([C:7](=[O:25])[CH2:8][C:9]2[CH:10]=[N:11][CH:12]=[C:13]([C:15]3[CH:16]=[N:17][C:18]4[NH:19][CH2:20][CH2:21][CH2:22][C:23]=4[CH:24]=3)[CH:14]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[C:32](Cl)(=[O:34])[CH3:33]>C(Cl)Cl.CCOC(C)=O>[C:32]([N:19]1[C:18]2[N:17]=[CH:16][C:15]([C:13]3[CH:14]=[C:9]([CH2:8][C:7]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[O:25])[CH:10]=[N:11][CH:12]=3)=[CH:24][C:23]=2[CH2:22][CH2:21][CH2:20]1)(=[O:34])[CH3:33]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 117667645HCID 117667645, compound

Product 1

HCID 117667658HCID 117667658, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Morpholin-4-yl-2-[5-(5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-pyridin-3-yl]-ethanone (62.4 mg, 0.184 mmol) is dissolved in DCM (2 mL). Pyridine (0.089 mL, 1.11 mmol) is added. Acetyl chloride (1.0M in DCM, 0.55 mL, 0.55 mmol) is added dropwise and the mixture is stirred for 16 h. The mixture is diluted with EtOAc (50 mL), washed with water (3×5 mL), and brine, dried over sodium sulfate, filtered, and concentrated. The resulting crude product is purified by normal phase chromatography using 0-6% MeOH in DCM as the gradient to afford the title compound.

Workup

  1. washwashed with water (3×5 mL), and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting crude product is purified by normal phase chromatography

Sources & evidence

ORD record
ord-0546ba65d75b427abb3e5d72690f6079
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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