Hydrochloric Acid → HCID 178429422, compound

HRID 2267337Notes

Reaction equation

HRID 2267337 reaction equation
[CH3:1][C:2]1([CH3:41])[N:6]([CH2:7][CH2:8][NH:9][C:10]2[N:15]=[C:14]([C:16]3[S:17][C:18]([S:21]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)(=[O:23])=[O:22])=[CH:19][CH:20]=3)[C:13]([C:31]3[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=3)[C:34]#[N:35])=[CH:12][N:11]=2)[C:5](=[O:39])[NH:4][C:3]1=[O:40].C[Si]([N:46]=[N+:47]=[N-:48])(C)C.C([Sn](=O)CCCC)CCC.Cl.C(=O)(O)[O-].[Na+]>CN(C)C=O>[NH:46]1[C:34]([C:33]2[CH:32]=[C:31]([C:13]3[C:14]([C:16]4[S:17][C:18]([S:21]([C:24]5[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=5)(=[O:23])=[O:22])=[CH:19][CH:20]=4)=[N:15][C:10]([NH:9][CH2:8][CH2:7][N:6]4[C:2]([CH3:41])([CH3:1])[C:3](=[O:40])[NH:4][C:5]4=[O:39])=[N:11][CH:12]=3)[CH:38]=[CH:37][CH:36]=2)=[N:35][N:48]=[N:47]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 516892Sodium BicarbonateHCID 60204452HCID 60204452, compound

Product 1

HCID 178429422HCID 178429422, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-(2-(2-(5,5-dimethyl-2,4-dioxoimidazolidin-1-yl)ethylamino)-4-(5-(4-fluorophenylsulfonyl)thiophen-2-yl)pyrimidin-5-yl)benzonitrile (110 mg, 0.19 mmol), trimethylsilyl azide (178 mg, 1.52 mmol) and dibutyltin oxide (47 mg, 0.19 mmol) in N,N-dimethylformamide (5 mL) was heated at 120° C. for 24 h. After cooling to rt, 10 mL of aqueous hydrochloric acid (10%) was added and the resulting mixture was stirred for 30 min. Saturated sodium bicarbonate was added to adjust to pH 5 and the mixture was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (3×50 mL), dried over anhydrous sodium sulfate and filtered. The solvent was removed in vacuo and the product purified by flash chromatography eluting with methanol (containing 10% acetic acid)/dichloromethane (1:20). MS (M+H)+ 634.

Workup

  1. temperatureAfter cooling to rt
  2. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  3. washThe combined organic layers were washed with brine (3×50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo
  7. customthe product purified by flash chromatography
  8. washeluting with methanol (containing 10% acetic acid)/dichloromethane (1:20)

Sources & evidence

ORD record
ord-df7a579bfe4242ea8ceb7c494cae5012
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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