1,1'-Carbonyldiimidazole → HCID 178517558, compound

HRID 1772700Notes

Reaction equation

HRID 1772700 reaction equation
[OH:1]/[N:2]=[C:3](/[C:5]1[N:10]2[CH:11]=[C:12]([CH2:14][O:15][C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]=3)[N:13]=[C:9]2[C:8]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[N:7][CH:6]=1)\[NH2:4].[C:32](N1C=CN=C1)(N1C=CN=C1)=[O:33].N12CCCN=C1CCCCC2>C(#N)C.CCOC(C)=O>[O:29]1[CH2:30][CH2:31][N:26]([C:8]2[C:9]3[N:10]([CH:11]=[C:12]([CH2:14][O:15][C:16]4[CH:25]=[CH:24][C:23]5[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=5)[N:17]=4)[N:13]=3)[C:5]([C:3]3[N:4]=[C:32]([OH:33])[O:1][N:2]=3)=[CH:6][N:7]=2)[CH2:27][CH2:28]1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 136942070HCID 136942070, compound

Product 1

HCID 178517558HCID 178517558, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of compound 55b (70.0 mg, 0.170 mmol), 1,1′-carbonyldiimidazole (40.6 mg, 0.250 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.099 mL, 0.670 mmol) in acetonitrile (2 mL) was stirred at rt for 12 h. The residue was diluted with EtOAc (2×50 mL) and washed with 1N HCl (30 mL). The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was triturated with MeOH, collected by filtration, and dried to give the title compound 75 as a yellow solid. 1H-NMR (400 MHz, CDCl3) δ (ppm): 3.79-3.96 (m, 4H), 4.49 (br. s., 4H), 5.66-5.76 (m, 2H), 6.99 (d, J=8.8 Hz, 1H), 7.36-7.47 (m, 1H), 7.66 (td, J=7.7, 1.2 Hz, 1H), 7.74 (d, J=8.1 Hz, 1H), 7.81 (s, 1H), 7.91 (d, J=8.3 Hz, 1H), 8.03 (d, J=8.8 Hz, 1H), 8.76 (s, 1H). Mass Spectrum (LCMS, ESI pos.) Calcd. for C22H19N7O4: 446.2 [M+H]. found 446.2.

Workup

  1. washwashed with 1N HCl (30 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated with MeOH
  7. filtrationcollected by filtration
  8. customdried

Sources & evidence

ORD record
ord-e6759f52b4804e4ca5a53b7a9a33cd00
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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