Benzylamine → HCID 10470300, compound

HRID 646664Notes

Reaction equation

HRID 646664 reaction equation
[NH2:1][C:2]1[C:3]([C:14]([OH:16])=O)=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:7]=1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.[CH2:46]([NH2:53])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>ClCCl.C(OCC)(=O)C>[NH2:1][C:2]1[C:3]([C:14]([NH:53][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[O:16])=[N:4][C:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][N:7]=1

Participants

8

Reactant 5

HCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12841582HCID 12841582, compound

Product 1

HCID 10470300HCID 10470300, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-amino-6-phenylpyrazine carboxylic acid (0.10 g, 0.47 mmol) in dichloromethane (3 mL) were added 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 0.11 g, 0.56 mmol), 1-hydroxybenzotriazole (HOBT, 75 mg, 0.56 mmol), and N-methylmorpholine (NMM, 56 mg, 0.56 mmol) at room temperature. The reaction was stirred for 15 min before benzylamine (0.56 mmol) was added. The reaction mixture was allowed to stir overnight. The reaction was diluted with ethyl acetate (200 mL) and washed with water (50 mL), saturated aqueous sodium bicarbonate (40 mL) and aqueous hydrochloric acid (30 mL), and saturated aqueous sodium chloride (25 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated at reduced pressure to afford product (91 mg, 67% yield) as light yellow solid: 1H NMR (400 MHz, CDCl3): δ 8.62 (s, 1H), 8.38 (br s, 1H), 7.84 (dd, 2H), 7.45 (m, 2H), 7.38 (m, 6H), 4.70 (d, 2H); MS (EI) for C18H16N4O: 305 (MH+).

Workup

  1. additionwas added
  2. washwashed with water (50 mL), saturated aqueous sodium bicarbonate (40 mL) and aqueous hydrochloric acid (30 mL), and saturated aqueous sodium chloride (25 mL)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-71c3f0ca495f4c9ca2877436bf4759ca
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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