Hydrochloric Acid → HCID 58337495, compound

HRID 1887435Notes

Reaction equation

HRID 1887435 reaction equation
N(OC(C)(C)C)=O.N[C:9]1[CH:10]=[C:11]([NH:22][C:23](=[O:31])[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=2)[CH:12]=[C:13]([O:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:14]=1.[ClH:32]>C(#N)C>[Cl:30][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[C:23]([NH:22][C:11]1[CH:12]=[C:13]([O:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:14]=[C:9]([Cl:32])[CH:10]=1)=[O:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 811100HCID 811100, compound

Product 1

HCID 58337495HCID 58337495, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
55 °C

Procedure

CuCl2 (47.5 mg, 0.353 mmol, 1.20 eq) was dissolved in acetonitrile (2 mL) in a flame-dried 3-neck flask flushed with argon and equipped with a condenser. t-Butyl nitrite (45.5 mg, 0.441 mmol, 1.50 eq) was added and the reaction heated at 55° C. Compound 2 (100 mg, 0.294 mmol, 1.00 eq) was dissolved in acetonitrile (0.1 mL) and added dropwise to the reaction. After 10 minutes the reaction was cooled to rt, poured into 20% HCl and extracted with CH2Cl2 (3×). The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 67 mg (63%) of the title compound as a pale yellow solid: 1H NMR (400 MHz, DMSO-d6) 10.50 (s, 1H), 8.47 (d, J=2.8 Hz, 1H), 8.45 (dd, J=4.6, 1.3 Hz, 1H), 7.96 (t, J=1.8 Hz, 1H), 7.86 (dt, J=7.9, 1.2 Hz, 1H), 7.77 (t, J=1.8 Hz, 1H), 7.68-7.66 (m, 1H), 7.58 (ddd, J=8.4, 3.0, 1.5 Hz, 1H), 7.56 (t, J=7.9 Hz, 1H), 7.48 (dd, J=8.4, 4.6 Hz, 1H), 7.40 (t, J=2.0 Hz, 1H), 6.94 (t, J=2.0 Hz, 1H); ES-MS [M+1]+: 359.0.

Workup

  1. customflushed with argon
  2. customequipped with a condenser
  3. additionadded dropwise to the reaction
  4. temperatureAfter 10 minutes the reaction was cooled to rt
  5. extractionextracted with CH2Cl2 (3×)
  6. dry with materialThe combined organics were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-7ed59e1cd40e4bce804e9f1895ff2fd3
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

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