Pyridine → HCID 57685257, compound

HRID 1926691Notes

Reaction equation

HRID 1926691 reaction equation
C(N1CCN(CC2C=CC(NC(=O)C3C=CC(C)=C([N+]([O-])=[O:26])C=3)=CC=2C(F)(F)F)CC1)C.N1C=CC=CC=1.[CH3:39][NH:40][C:41]1[C:42]2[CH:49]=[CH:48][N:47]([S:50]([C:53]3[CH:58]=[CH:57][C:56]([CH3:59])=[CH:55][CH:54]=3)(=[O:52])=[O:51])[C:43]=2[N:44]=[CH:45][N:46]=1.Cl[CH2:61][Cl:62]>>[Cl:62][C:61]([N:40]([C:41]1[C:42]2[CH:49]=[CH:48][N:47]([S:50]([C:53]3[CH:58]=[CH:57][C:56]([CH3:59])=[CH:55][CH:54]=3)(=[O:51])=[O:52])[C:43]=2[N:44]=[CH:45][N:46]=1)[CH3:39])=[O:26]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 57685258N-Methyl-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amineHCID 59346396HCID 59346396, compound

Product 1

HCID 57685257HCID 57685257, compound

Procedure

To a solution of 3 (3.45 g, 8.2 mmol, 1.0 eq.),) and pyridine (0.66 ml, 0.82 mmol, 1.0 eq.),) in dichloromethane (40 ml) at 23° C. is added carbamoyl chloride 6 (3 g, 8.2 mmol, 1.0 eq.) drop wise over a period of 15 minutes. The reaction mixture is further stirred at room temperature for a period of 8 hours after which, it is partitioned between dichloromethane and water. The organic layer is separated and the aqueous layer is extracted with dichloromethane. The combined organic extracts are washed with water, dried over Na2SO4, filtered and concentrated to provide crude product 7. The residue is purified using column chromatography with MeOH/CH2Cl2 (5:1) as eluent to afford the title product 7.

Workup

  1. customis partitioned between dichloromethane and water
  2. customThe organic layer is separated
  3. extractionthe aqueous layer is extracted with dichloromethane
  4. washThe combined organic extracts are washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3c3a67b26afe484a9c91f4f97e685c16
Source dataset
uspto-grants-2012_05
Patent number
US08183248B2

Reaction notes

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