Morpholine → 3-[5-Amino-6-(morpholin-4-ylmethyl)pyrazin-2-yl]-N-(phenylmethyl)benzamiide

HRID 646771Notes

Reaction equation

HRID 646771 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:10]2[CH:11]=[C:12]([CH:23]=[CH:24][CH:25]=2)[C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])=[N:6][C:7]=1[CH:8]=O.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.[BH-](O[C:42]([CH3:44])=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C.C(=O)([O-])[O-].[Na+].[Na+]>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:10]2[CH:11]=[C:12]([CH:23]=[CH:24][CH:25]=2)[C:13]([N:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:44]2[CH:42]=[CH:25][CH:10]=[CH:5][CH:4]=2)=[O:14])=[N:6][C:7]=1[CH2:8][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 866078513-(5-Amino-6-formylpyrazin-2-yl)-N-benzylbenzamide

Product 1

HCID 866078523-[5-Amino-6-(morpholin-4-ylmethyl)pyrazin-2-yl]-N-(phenylmethyl)benzamiideYield 153.5%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

3-(5-Amino-6-formylpyrazin-2-yl)-N-benzylbenzamide (1.27 g, 3.83 mmol) was dissolved in dichloroethane (30 mL) at 0° C. Morpholine (400 mg, 4.6 mmol), and NaBH(OAc)3 (2.03 g, 9.58 mmol) were added and the reaction was stirred at room temperature for 20 h. The reaction mixture was diluted with saturated sodium carbonate and extracted 3× with ethyl acetate. The combined ethyl acetate layers were dried over sodium sulfate, filtered, and concentrated iii vacuo to afford the product (1.41 g, 88% yield). 1H NMR (400 MHz, d4-CD3OD): δ 8.60 (s, 1H), 8.47 (t, 1H), 8.12 (m, 1H), 7.84 (m, 1H), 7.55 (t, 1H), 7.31-7.89 (m, 4H), 7.23-7.26 (m, 1H), 4.61 (s, 2H), 4.43 (s, 2H), 3.32-4.16 (m, 8H). MS (EI) for C23H25N5O2: 404 (MH+).

Workup

  1. extractionextracted 3× with ethyl acetate
  2. dry with materialThe combined ethyl acetate layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated iii vacuo

Sources & evidence

ORD record
ord-28fdc55057b447cb92976b59a774729b
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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