HCID 56593553, compound → HCID 56847714, compound

HRID 510089Notes

Reaction equation

HRID 510089 reaction equation
[NH2:1][C:2]1[C:7]([N:8]([CH2:13][C:14]([F:17])([F:16])[F:15])[C:9](=O)[O:10]C)=[C:6]([NH2:18])[N:5]=[C:4]([C:19]2[C:27]3[C:22](=[N:23][CH:24]=[CH:25][CH:26]=3)[N:21]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[F:35])[N:20]=2)[N:3]=1>O1CCCC1>[NH2:1][C:2]1[N:3]=[C:4]([C:19]2[C:27]3[C:22](=[N:23][CH:24]=[CH:25][CH:26]=3)[N:21]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[F:35])[N:20]=2)[N:5]=[C:6]2[C:7]=1[N:8]([CH2:13][C:14]([F:15])([F:16])[F:17])[C:9](=[O:10])[NH:18]2

Participants

3

Reactant 1

HCID 56593553HCID 56593553, compound

Product 1

HCID 56847714HCID 56847714, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Under an argon atmosphere, 2.100 g (4.282 mmol) of the compound from example 15A were dissolved in 235 ml of tetrahydrofuran and cooled to 0° C., and 10.705 ml (10.705 mmol) of a 1N solution of bis(trimethylsilyl)sodium amide in tetrahydrofuran were added dropwise. The mixture was stirred at 0° C. for 2 h and then at RT for 16 h. The tetrahydrofuran was partly concentrated in an argon stream and the precipitate was filtered off. 1.290 g of the title compound were obtained (66% of theory).

Workup

  1. waitat RT for 16 h
  2. concentrationThe tetrahydrofuran was partly concentrated in an argon stream
  3. filtrationthe precipitate was filtered off

Sources & evidence

ORD record
ord-adadcd8e220147d0a9c9212ddb803b87
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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