1,2-Dichloroethane → HCID 69268257, compound

HRID 2055575Notes

Reaction equation

HRID 2055575 reaction equation
C(N(CC)CC)C.FC(F)(F)S(OC1C(F)=CC=CC=1[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH:28][C:29]([C:31]2([NH:34][C:35]([C:37]3[CH:38]=[N:39][CH:40]=[N:41][CH:42]=3)=[O:36])[CH2:33][CH2:32]2)=[O:30])=[C:23]([F:43])[CH:22]=1)(=O)=O.[Cl-].[Br:47]C1C=CC(C[NH3+])=C(F)C=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1>C(Cl)Cl.O>[Br:47][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH:28][C:29]([C:31]2([NH:34][C:35]([C:37]3[CH:38]=[N:39][CH:40]=[N:41][CH:42]=3)=[O:36])[CH2:33][CH2:32]2)=[O:30])=[C:23]([F:43])[CH:22]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 181649HOAtHCID 11307452HCID 11307452, compoundHCID 45075641147181-08-6

Product 1

HCID 69268257HCID 69268257, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.036 g, 10.24 mmol) was added to a stirred solution of the compound of reference Example 3 (2.556 g, 10.24 mmol), (4-bromo-2-fluorophenyl)methanaminium chloride (2.463 g, 10.24 mmol), EDC (1.963 g, 10.24 mmol), and HOAT (0.418 g, 3.072 mmol) in CH2Cl2 (25 mL). After 1 h, the reaction was diluted with water and extracted with ethyl acetate. The organic extract was washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure to yield a yellow solid. This solid was purified by silica gel chromatography, eluting with 5% methanol/CH2Cl2 to yield N-(1-{[(4-bromo-2-fluorobenzyl)amino]carbonyl}cyclopropyl)pyrimidine-5-carboxamide as a white solid. Low resolution MS: (M+H+)=393.03.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto yield a yellow solid
  8. customThis solid was purified by silica gel chromatography
  9. washeluting with 5% methanol/CH2Cl2

Sources & evidence

ORD record
ord-242e30932d214545b494277a7299ca75
Source dataset
uspto-grants-2008_02
Patent number
US07332499B2

Reaction notes

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