HCID 68648142, compound → HCID 136174013, compound

HRID 1162094Notes

Reaction equation

HRID 1162094 reaction equation
C[Si](C)(C)CCOC[N:7]1[CH:11]=[C:10]([C:12]2[N:16]3[N:17]=[C:18]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[CH:19]=[CH:20][C:15]3=[N:14][CH:13]=2)[CH:9]=[N:8]1>C(O)(C(F)(F)F)=O.O>[NH:8]1[CH:9]=[C:10]([C:12]2[N:16]3[N:17]=[C:18]([N:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)[CH:19]=[CH:20][C:15]3=[N:14][CH:13]=2)[CH:11]=[N:7]1

Participants

4

Reactant 1

HCID 68648142HCID 68648142, compound

Product 1

HCID 136174013HCID 136174013, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The product from step C (284 mg, 0.71 mmol) was heated to 60° C. in a mixture of TFA (5 mL) and water (1 mL) for 1 h. Upon cooling the reaction mixture was concentrated and partitioned between ethyl acetate and saturated sodium carbonate solution. The solid that formed at the solvent interface was removed by filtration and dried under vacuum to provide the pure title compound (63 mg, 33%) as a white solid: 1H NMR (500 MHz, DMSO-d6) δ 11.02 (s, 1H), 8.40 (s, 1H), 8.17 (s, 1H), 7.89 (d, J=9.9 Hz, 1H), 7.84 (s, 1H), 7.15 (d, J=9.9 Hz, 1H), 3.79 (t, J=3.9 Hz, 4H), 3.52 (t, J=4.3 Hz, 4H); 13C NMR (125 MHz, DMSO-d6) δ 155.2, 136.1, 135.8, 128.4, 125.8, 125.1, 121.8, 109.2, 108.6, 65.6, 46.0; HPLC tR=13.6 min (Luna), >99%; ES-MS: (M+H)=271 m/z.

Workup

  1. temperatureUpon cooling the reaction mixture
  2. concentrationwas concentrated
  3. custompartitioned between ethyl acetate and saturated sodium carbonate solution
  4. customThe solid that formed at the solvent interface
  5. customwas removed by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-268de7ac6b0f4f96be1cdea0725728d2
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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