Iodine chloride → HCID 178511641, compound

HRID 226001Notes

Reaction equation

HRID 226001 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=3)[N:12]3[N:24]=[CH:25][CH:26]=[C:11]3[N:10]=2)[CH2:4][CH2:3]1.[I:27]Cl>C(Cl)Cl>[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=3)[N:12]3[N:24]=[CH:25][C:26]([I:27])=[C:11]3[N:10]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 178511640HCID 178511640, compound

Product 1

HCID 178511641HCID 178511641, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of {5-[(trans-4-aminocyclohexyl)amino](pyrazolo[1,5-a]pyrimidin-7-yl)}[(3-chlorophenyl)methyl]amine (41.8 mg) in CH2Cl2 (565 μL) was added ICl (169 μL, 1.0 M in CH2Cl2), and the resulting mixture was stirred at room temperature for 4 h in the dark. The reaction was quenched with saturated aqueous Na2S2O3. The resulting precipitate was collected by filtration. After extraction of filtrate by CH2Cl2, the combined organic layer was washed with saturated aqueous NaCl. To this solution, the precipitate collected above was dissolved, and the solvent was removed in vacuo. The residue was purified by preparative HPLC, and the fraction contained the title compound was basified (pH 9) with saturated aqueous NaHCO3. After extraction with CH2Cl2, combined organic layer was dried over Na2SO4. The solvent was removed in vacuo, and the title compound (23.11 mg, 41% yield) was obtained as a white solid. The 1H-NMR, HPLC retention time and ESI/MS data for this compound are shown below.

Workup

  1. customThe reaction was quenched with saturated aqueous Na2S2O3
  2. filtrationThe resulting precipitate was collected by filtration
  3. extractionAfter extraction of filtrate by CH2Cl2
  4. washthe combined organic layer was washed with saturated aqueous NaCl
  5. customTo this solution, the precipitate collected above
  6. dissolutionwas dissolved
  7. customthe solvent was removed in vacuo
  8. customThe residue was purified by preparative HPLC
  9. extractionAfter extraction with CH2Cl2
  10. dry with materialwas dried over Na2SO4
  11. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-60f0a53a129c42b2aac60c3dce251565
Source dataset
uspto-grants-2009_07
Patent number
US07557110B2

Reaction notes

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