Water → HCID 117728682, compound

HRID 718643Notes

Reaction equation

HRID 718643 reaction equation
[OH:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]3[N:17]=[CH:18][CH:19]=[C:20]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[C:15]3=[N:14][C:13]=2[CH2:27][CH2:28][C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[N:30]=2)=[CH:8][CH:7]=1)[C:3]([O-:5])=O.ClC(Cl)(Cl)[C:41]([N:43]=C=O)=[O:42].O>ClCCl.C(O)C>[O:24]1[CH2:23][CH2:22][N:21]([C:20]2[C:15]3[N:16]([C:12]([C:9]4[CH:10]=[CH:11][C:6]([CH:2]5[O:1][C:41](=[O:42])[NH:43][C:3]5=[O:5])=[CH:7][CH:8]=4)=[C:13]([CH2:27][CH2:28][C:29]4[CH:38]=[CH:37][C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[N:30]=4)[N:14]=3)[N:17]=[CH:18][CH:19]=2)[CH2:26][CH2:25]1

Participants

6

Reactant 3

HCID 962WaterHCID 76400Trichloroacetyl isocyanateHCID 131734174HCID 131734174, compound

Product 1

HCID 117728682HCID 117728682, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of compound 50c (0.15 g, 0.29 mmol) and 2,2,2-trichloroacetyl isocyanate (81 mg, 0.43 mmol) in dichloromethane (10 mL) was stirred at rt for 30 min and concentrated in vacuo. The residue obtained was dissolved in ethanol (10 mL), and TEA (87 mg, 0.86 mmol) was added. The reaction mixture was heated at reflux for 2 h and allowed to cool to rt. Water (10 mL) was added. The solids formed were collected by filtration and washed with Et2O (2×20 mL) to obtain the title compound 70 as a yellow solid. 1H-NMR (300 MHz, DMSO-d6+D2O) δ (ppm): 8.17 (d, J=8.4 Hz, 1H), 8.00 (d, J=5.4 Hz, 1H), 7.88 (d, J=8.1 Hz, 2H), 7.70 (t, J=7.8 Hz, 1H), 7.54-7.48 (m, 3H), 7.37-7.31 (m, 3H), 6.27 (d, J=5.7 Hz, 1H), 5.27 (s, 1H), 3.90-3.73 (m, 4H), 3.68-3.56 (m, 4H), 3.34-3.28 (m, 4H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C30H26N6O4: 535.2 (M+H). Found: 535.2.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue obtained
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 2 h
  5. customThe solids formed
  6. filtrationwere collected by filtration
  7. washwashed with Et2O (2×20 mL)

Sources & evidence

ORD record
ord-27714cff143d4b928b9947869d33016b
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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