Triethylamine → HCID 90014402, compound

HRID 711295Notes

Reaction equation

HRID 711295 reaction equation
FC(F)(F)S(C1C=CC(N)=CC=1)(=O)=O.C(N(CC)CC)C.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.[F:34][C:35]([F:50])([F:49])[S:36]([C:39]1[CH:44]=[CH:43][C:42]([NH:45][C:46](Cl)=[O:47])=[CH:41][CH:40]=1)(=[O:38])=[O:37].[CH3:51][Si:52]([CH3:72])([CH3:71])[CH2:53][CH2:54][O:55][CH2:56][N:57]1[C:61]2=[N:62][CH:63]=[CH:64][CH:65]=[C:60]2[C:59]([CH2:66][NH:67][CH:68]([CH3:70])[CH3:69])=[CH:58]1>>[CH3:70][CH:68]([N:67]([CH2:66][C:59]1[C:60]2[C:61](=[N:62][CH:63]=[CH:64][CH:65]=2)[N:57]([CH2:56][O:55][CH2:54][CH2:53][Si:52]([CH3:71])([CH3:51])[CH3:72])[CH:58]=1)[C:46]([NH:45][C:42]1[CH:43]=[CH:44][C:39]([S:36]([C:35]([F:50])([F:49])[F:34])(=[O:38])=[O:37])=[CH:40][CH:41]=1)=[O:47])[CH3:69]

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 1363154-Aminophenyl trifluoromethyl sulphoneHCID 90014273HCID 90014273, compoundHCID 90014312HCID 90014312, compound

Product 1

HCID 90014402HCID 90014402, compoundYield 38%

Procedure

To a solution of 4-[(trifluoromethyl)sulfonyl]aniline (180 mg, 0.80 mmol) in 2 mL dichlroethane at 0° C. was added triethylamine (0.250 mL, 1.76 mmol) and triphosgene (71 mg, 0.24 mmol). The solution was allowed to stir at ambient temperature for 10 min. To the crude reaction mixture of {4-[(trifluoromethyl)sulfonyl]phenyl}carbamic chloride was added N-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-3-yl)methyl]propan-2-amine (256 mg, 0.80 mmol) and the reaction was allowed to stir at ambient temperature for 16 h. The mixture was concentrated and partitioned between saturated NaHCO3 and ethylacetate. The organics were washed with water and brine, then dried over Na2SO4, filtered and concentrated. The filtrate was concentrated and purified by silica gel chromatography to give 1-propan-2-yl-3-{4-[(trifluoromethyl)sulfonyl]phenyl}-1-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-3-yl)methyl]urea (38%). LCMS [M+H]+=571.2.

Workup

  1. stirringto stir at ambient temperature for 16 h
  2. concentrationThe mixture was concentrated
  3. custompartitioned between saturated NaHCO3 and ethylacetate
  4. washThe organics were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. concentrationThe filtrate was concentrated
  9. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-e836ec9a95a645d0b6231eded8c9361c
Source dataset
uspto-grants-2015_11
Patent number
US09181261B2

Reaction notes

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