Dichloromethane → HCID 86685338, compound

HRID 1853081Notes

Reaction equation

HRID 1853081 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]([C:13]3[CH:14]=[N:15][N:16]([C:18]4([CH2:29][C:30]#[N:31])[CH2:21][N:20]([S:22]([C:25]([F:28])([F:27])[F:26])(=[O:24])=[O:23])[CH2:19]4)[CH:17]=3)[N:10]3[CH:32]=[CH:33][N:34]=[C:9]3[CH:8]=2)[CH:4]=[N:3]1.C([O-])(O)=O.[Na+].C(Cl)[Cl:41]>>[Cl:41][C:32]1[N:10]2[C:11]([C:13]3[CH:14]=[N:15][N:16]([C:18]4([CH2:29][C:30]#[N:31])[CH2:21][N:20]([S:22]([C:25]([F:28])([F:26])[F:27])(=[O:24])=[O:23])[CH2:19]4)[CH:17]=3)=[N:12][C:7]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)=[CH:8][C:9]2=[N:34][CH:33]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 53467643HCID 53467643, compound

Product 1

HCID 86685338HCID 86685338, compoundYield 17%

Procedure

2-(3-(4-(7-(1-Methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-1-(trifluoromethylsulfonyl)azetidin-3-yl)acetonitrile (Example 96; 0.150 g, 0.305 mmol) was suspended in DCM (5 mL) and saturated aqueous NaHCO3 (2 mL). n-Chlorosuccinimide (0.204 g, 1.53 mmol) was added in one portion and the reaction mixture stirred at ambient temperature overnight. The reaction mixture was partitioned between saturated aqueous NaHCO3 and DCM. The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure to afford the crude material, which was purified by flash column chromatography, eluting with 2-3% (9:1 MeOH:NH4OH)/DCM to provide 2-(3-(4-(3-chloro-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-1-(trifluoromethylsulfonyl)azetidin-3-yl)acetonitrile (0.027 g, 0.051 mmol, 17% yield). MS (apci) m/z=526.0 (M+H).

Workup

  1. customThe reaction mixture was partitioned between saturated aqueous NaHCO3 and DCM
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude material, which
  7. customwas purified by flash column chromatography
  8. washeluting with 2-3% (9:1 MeOH:NH4OH)/DCM

Sources & evidence

ORD record
ord-09c530a9012e41b89d0a36e29c803e2b
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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