Water → HCID 178505632, compound

HRID 510134Notes

Reaction equation

HRID 510134 reaction equation
N(OC(C)(C)C)=O.[F:8][C:9]1[CH:34]=[CH:33][CH:32]=[CH:31][C:10]=1[CH2:11][N:12]1[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[C:14]([C:21]2[N:22]=[C:23](N)[C:24]3[N:29]=[N:28][NH:27][C:25]=3[N:26]=2)=[N:13]1.O>CN(C)C=O>[F:8][C:9]1[CH:34]=[CH:33][CH:32]=[CH:31][C:10]=1[CH2:11][N:12]1[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[C:14]([C:21]2[N:22]=[CH:23][C:24]3[N:29]=[N:28][NH:27][C:25]=3[N:26]=2)=[N:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 10906Tert-Butyl nitriteHCID 178508324HCID 178508324, compound

Product 1

HCID 178505632HCID 178505632, compoundYield 1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
65 °C

Procedure

570 mg (5.535 mmol) of tert-butyl nitrite were dissolved in 20 ml of dry dimethylformamide, and 1000 mg (2.767 mmol) of the compound from example 53 suspended in 15 ml of dimethylformamide were added at 65° C. by means of a syringe pump within 1 h. After stirring at 65° C. for a further hour, 100 ml of water were added, forming a precipitate. The precipitate was filtered off and purified by means of preparative HPLC (eluent: water/acetonitrile/water with 1% trifluoroacetic acid, gradient 64:20:16→0:100:0). 10 mg of the title compound were obtained (1% of theory).

Workup

  1. additionwere added at 65° C. by means of a syringe pump within 1 h
  2. customforming a precipitate
  3. filtrationThe precipitate was filtered off
  4. custompurified by means of preparative HPLC (eluent: water/acetonitrile/water with 1% trifluoroacetic acid, gradient 64:20:16→0:100:0)

Sources & evidence

ORD record
ord-aacaab3454e941e998c2b8e45ad9eaa1
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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