Water → HCID 66614113, compound

HRID 510088Notes

Reaction equation

HRID 510088 reaction equation
[NH2:1][C:2]1[C:7](CCNC(=O)OC)=[C:6]([NH2:15])[N:5]=[C:4]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])[N:17]=2)[N:3]=1.[OH2:33]>O1CCCC1>[NH2:1][C:2]1[N:3]=[C:4]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])[N:17]=2)[N:5]=[C:6]2[C:7]=1[N:3]([CH2:2][CH3:7])[C:4](=[O:33])[NH:15]2

Participants

4

Reactant 2

HCID 962WaterHCID 86720051HCID 86720051, compound

Product 1

HCID 66614113HCID 66614113, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

59 mg (0.135 mmol) of the compound from example 14A were dissolved in 7.5 ml of tetrahydrofuran and cooled to 0° C., and 150 μl (0.150 mmol) of a 1N solution of bis(trimethylsilyl)sodium amide in tetrahydrofuran were added dropwise. The mixture was stirred at 0° C. for 3 h and then at RT for 16 h. Another 150 μl (0.150 mmol) of a 1N solution of bis(trimethylsilyl)sodium amide in tetrahydrofuran were added dropwise and the mixture was stirred at RT for 2 days. Water was added and the reaction mixture was concentrated under reduced pressure and the residue was purified by means of preparative HPLC (eluent: methanol/water, gradient 30:70→90:10). 29 mg of the title compound were obtained (53% of theory).

Workup

  1. waitat RT for 16 h
  2. stirringthe mixture was stirred at RT for 2 days
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by means of preparative HPLC (eluent: methanol/water, gradient 30:70→90:10)

Sources & evidence

ORD record
ord-abf294be15aa490f979c633ee062cfad
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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