Water → HCID 66614084, compound

HRID 510090Notes

Reaction equation

HRID 510090 reaction equation
N(OC(C)(C)C)=O.N[C:9]1[N:17]=[C:16]([C:18]2[C:26]3[C:21](=[N:22][CH:23]=[CH:24][CH:25]=3)[N:20]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[F:34])[N:19]=2)[N:15]=[C:14]2[C:10]=1[N:11]([CH2:36][C:37]([F:40])([F:39])[F:38])[C:12](=[O:35])[NH:13]2.O>CN(C)C=O>[F:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[CH2:27][N:20]1[C:21]2=[N:22][CH:23]=[CH:24][CH:25]=[C:26]2[C:18]([C:16]2[N:15]=[C:14]3[C:10]([N:11]([CH2:36][C:37]([F:38])([F:39])[F:40])[C:12](=[O:35])[NH:13]3)=[CH:9][N:17]=2)=[N:19]1

Participants

5

Reactant 3

HCID 962WaterHCID 10906Tert-Butyl nitriteHCID 56847714HCID 56847714, compound

Product 1

HCID 66614084HCID 66614084, compoundYield 10.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
65 °C

Procedure

447 mg (4.337 mmol) of tert-butyl nitrite were dissolved in 20 ml of dry dimethylformamide, and 994 mg (2.169 mmol) of the compound from example 44 dissolved 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, 40 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 68:15:17→0:100:0). 99 mg of the title compound were obtained (10% 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 68:15:17→0:100:0)

Sources & evidence

ORD record
ord-1044fefbf3bd4f7283f018049234fcc0
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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