Hydrochloric Acid → HCID 58266426, compound

HRID 1888391Notes

Reaction equation

HRID 1888391 reaction equation
FC(F)(S([O:16][S:17]([C:20]([F:32])([F:31])[C:21]([F:30])([F:29])[C:22]([F:28])([F:27])[C:23]([F:26])([F:25])[F:24])(=[O:19])=[O:18])(=O)=O)C(F)(F)C(F)(F)C(F)(F)F.[C:34]1([S:40]([N:43]2[C:47]3[CH:48]=[N:49][C:50]([C:53]#[N:54])=[C:51](O)[C:46]=3[C:45]3[CH:55]=[C:56]([C:59]4[CH:60]=[N:61][N:62]([CH3:64])[CH:63]=4)[CH:57]=[N:58][C:44]2=3)(=[O:42])=[O:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.N1C=CC=CC=1.Cl>C(Cl)Cl>[C:34]1([S:40]([N:43]2[C:47]3[CH:48]=[N:49][C:50]([C:53]#[N:54])=[C:51]([O:16][S:17]([C:20]([F:31])([F:32])[C:21]([F:30])([F:29])[C:22]([F:27])([F:28])[C:23]([F:24])([F:25])[F:26])(=[O:18])=[O:19])[C:46]=3[C:45]3[CH:55]=[C:56]([C:59]4[CH:60]=[N:61][N:62]([CH3:64])[CH:63]=4)[CH:57]=[N:58][C:44]2=3)(=[O:41])=[O:42])[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 4281883Perfluorobutanesulfonic anhydrideHCID 582663859-Benzenesulfonyl-5-hydroxy-3-(1-methyl-1H-pyrazol-4-yl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

Product 1

HCID 58266426HCID 58266426, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1,2,2,3,3,4,4,4-Nonafluorobutanesulfonic anhydride (0.75 g, 0.40 mL, 1.3 mmol) was added dropwise to a suspension of 9-benzenesulfonyl-5-hydroxy-3-(1-methyl-1H-pyrazol-4-yl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (106 mg, 0.25 mmol) in pyridine (0.7 mL, 8.0 mmol) and dry DCM (7 mL) at 0° C. The reaction mixture was then allowed to warm to ambient temperature and stirred for 4 h. The reaction mixture was treated with 1N hydrochloric acid (6 mL) and the phases were separated. The aqueous phase was extracted with DCM (2×10 mL), the combined organic phase was dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant residue was purified by chromatography (silica, 2 g column, Si-SPE, gradient of DCM/EtOAc) and further trituration with pentane (2 mL) to afford the title compound as a white solid (150 mg, 84%). 1H NMR (CDCl3, 400 MHz): 9.95 (s, 1H), 8.99 (d, J=2.1 Hz, 1H), 8.74 (d, J=2.1 Hz, 1H), 8.35-8.32 (m, 2H), 7.86 (d, J=0.8 Hz, 1H), 7.74-7.68 (m, 2H), 7.61-7.56 (m, 2H), 4.04 (s, 3H). LCMS (Method G): RT=4.80 min, M+H+=713.

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with DCM (2×10 mL)
  3. dry with materialthe combined organic phase was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by chromatography (silica, 2 g column, Si-SPE, gradient of DCM/EtOAc) and further trituration with pentane (2 mL)

Sources & evidence

ORD record
ord-2d5b000d61f34ed6a01d85a5943a522e
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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