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HRID906639

反应详情

EQUATION

反应方程式

HRID 906639 的结构方程式

REACTANTS

反应物

5
结构：O=C(O)c1ccccc1O
HCID338

Salicylic acid

C7H6O3

结构：CCN=C=NCCCN(C)C
HCID15908

1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

C8H17N3

结构：CN1C(=O)CC(=O)N(C)C1=O
HCID69860

2,4,6(1H,3H,5H)-Pyrimidinetrione, 1,3-dimethyl-

C6H8N2O3

结构：On1nnc2ccccc21
HCID75771

1-Hydroxybenzotriazole

C6H5N3O

结构：C=CCN(CC=C)Cc1ccc(S(=O)(=O)N2CCC(Nc3cccc(S(=O)(=O)C(F)(F)F)c3)CC2)s1
HCID86761398

未命名化合物

PRODUCTS

生成物

1
结构：NC(=O)c1cccc(O)c1
HCID342403

3-hydroxybenzamide

C7H7NO2

AUXILIARIES

试剂、催化剂与溶剂

2
结构：c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1
催化剂HCID178418397

未命名化合物

结构：ClCCl
溶剂HCID6344

Dichloromethane

CH2Cl2

CONDITIONS

反应条件

温度
23 °C

PROCEDURE

实验过程

A solution of the bisallylamine 269c (1.15 g, 2.04 mmol), N,N′-dimethylbarbituric acid (NDMBA, 637 mg, 4.08 mmol), and Pd(PPh3)4 (110 mg, 0.096 mmol) in CH2Cl2 (20 mL) was degassed by bubbling argon for 10 min. The reaction was stirred at 23° C. over the week-end (3 d), concentrated, diluted with DMF (12 mL), and treated with salicylic acid (290 mg, 2.10 mmol), 1-hydroxybenzotriazole (HOBt, 283 mg, 2.10 mmol), and N-ethyl-N′-(3-dimethylaminopropyl)-carbodiimide (EDC, 402 mg, 2.10 mmol) for 24 h at 23° C. Dilution with EtOAc, washing (H2O, NaHCO3 sat., brine), drying (MgSO4), and evaporation afforded the crude 3-hydroxybenzamide. Purification by reverse-phase prep. HPLC (C8, H2O:CH3CN 60:40→0:100 over 40 min, r.t=23 min) and freeze-drying afforded 466 mg (38% from 269c) of the title 3-hydroxybenzamide as a white powder: NMR (DMSO-d6) δ 12.1 (s, 1H), 9.48 (t, J=5.9 Hz, 1H), 7.86 (dd, 7.9, 1.5 Hz, 1H), 7.50 (d, J=3.8 Hz, 1H), 7.45 (t, J=8.1 Hz, 1H), 7.41 (dd, J=8.9, 1.5 Hz, 1H), 7.21 (d, J=3.8 Hz, 1H), 7.18-7.10 (m, 3H), 6.93 (d, J=83 Hz, 1H), 6.91 (td, J=8.4, 1.1 Hz, 1H), 6.52 (d, J=7.7 Hz, 1H), 4.73 (d, J=5.8 Hz, 2H), 3.57-3.47 (br. d, 12.1, 2H), 3.52-3.35 (br. m., 1H), 2.62 (t, J=10.4 Hz, 2H), 2.07 (s, 1.2H, residual CH3CN), 2.02-1.92 (br. d, J=10.4 Hz, 2H), 1.47 (qd, 11.2, 3.6 Hz, 2H). 13C NMR (DMSO-d6) δ167.52 (s, C═O), 158.36 (s), 148.98 (s), 147.85 (s), 132.83 (d), 132.74 (s), 131.47 (d), 130.00 (d), 128.98 (s), 127.09 (d), 125.52 (d), 124.83 (s), 118.92 (q, residual CH3CN), 11834 (q, J=326 Hz, CF3), 117.75 (d), 116.24 (d), 115.23 (d), 114.19 (q), 111.33 (d), 45.93 (d), 43.66 (t), 36.66 (t), 29.18 (t), 0.00 (s, residual CH3CN). M/Z APCI: 604 (M+1), 602 (M−1). Anal. HPLC: R.t=6.60 min (method a). C24H24F3N3O6S3. 0.3 CH3CN 1.0 H2O Calc.: C, 47.53%. H, 4.36%. N, 7.44%. Found: C, 47.41%, H, 4.09%, N, 7.49%.

WORKUP

后处理

  1. customby bubbling argon for 10 min
  2. concentrationconcentrated
  3. additiondiluted with DMF (12 mL)
  4. washDilution with EtOAc, washing (H2O, NaHCO3 sat., brine)
  5. customdrying
  6. custom(MgSO4), and evaporation