Benzylamine → HCID 24958968, compound

HRID 2381850Notes

Reaction equation

HRID 2381850 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([N:16]2[CH:20]=[C:19]([C:21]([OH:23])=O)[N:18]=[N:17]2)=[N:13][C:12]=1[CH3:24])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C.[CH2:55]([NH2:62])[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1>CN(C)C=O.ClCCl>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([N:16]2[CH:20]=[C:19]([C:21](=[O:23])[NH:62][CH2:55][C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)[N:18]=[N:17]2)=[N:13][C:12]=1[CH3:24])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 7504BenzylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 68492838HCID 68492838, compound

Product 1

HCID 24958968HCID 24958968, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(5-(benzylcarbamoyl)-4-methylthiazol-2-yl)-1H-1,2,3-triazole-4-carboxylic acid (0.25 g, 0.73 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added 1-hydroxybenzotriazole (0.12 g, 0.87 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (0.17 g, 0.87 mmol), N,N-diisopropylethylamine (0.38 mL, 2.19 mmol) and benzylamine (0.095 mL, 0.87 mmol). The reaction mixture was stirred at ambient temperature for 18 hours, diluted with dichloromethane (30 mL) and washed with saturated aqueous sodium bicarbonate (15 mL) and brine (15 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography to afford the title compound as a white solid in 8% yield: mp 178-180° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 9.33 (t, J=6.0 Hz, 1H), 9.24 (s, 1H), 9.02 (t, J=6.0 Hz, 1H), 7.36-7.23 (m, 10H), 4.49-4.46 (m, 4H), 2.63 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 160.1, 158.4, 154.2, 152.4, 143.6, 139.1, 138.9, 128.3, 128.2, 127.3, 127.2, 126.9, 126.8, 125.3, 123.5, 42.8, 42.1, 17.1; MS (ES+) m/z 433.3 (M+1).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (15 mL) and brine (15 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c0aabb9cc7c9457298d70ad1be8988b9
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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