Dichloromethane → HCID 131723557, compound

HRID 991694Notes

Reaction equation

HRID 991694 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][CH2:12][CH2:13][O:14][C:15]3[C:16]([N:21]4[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]4)=[N:17][CH:18]=[CH:19][N:20]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O.C(Cl)[Cl:42]>>[ClH:42].[ClH:42].[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][CH2:12][CH2:13][O:14][C:15]3[C:16]([N:21]4[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]4)=[N:17][CH:18]=[CH:19][N:20]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 22036319HCID 22036319, compound

Product 1

HCID 131723557HCID 131723557, compoundYield 62%

Procedure

To a solution of the product obtained in Step 2 (0.43 g, 0.94 mmol) in CH2Cl2 (2 mL) was added CF3COOH (1.5 mL) at room temperature. The solution was stirred at room temperature for 5 h and evaporated to dryness. The residue was dissolved in EtOAc. The solution was washed with 25% aqueous NaOH and dried over K2CO3. A solution of HCl in Et2O was dropped into the solution until no more precipitate formed. The precipitate was collected, washed with ethyl ether, and dried in vacuum to give 251 mg (62%) of the title product: mp 158-160° C. MS m/z 358 (M)+. HRMS m/z calcd for C18H22N4O4 (M)+ 358.1641, found 358.1647.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in EtOAc
  3. washThe solution was washed with 25% aqueous NaOH
  4. dry with materialdried over K2CO3
  5. additionA solution of HCl in Et2O was dropped into the solution until no more precipitate
  6. customformed
  7. customThe precipitate was collected
  8. washwashed with ethyl ether
  9. customdried in vacuum

Sources & evidence

ORD record
ord-7c1b7e6ad5fc4ea3ba5276c84cddb5a3
Source dataset
uspto-grants-2002_10
Patent number
US06465467B1

Reaction notes

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