Trifluoroacetic anhydride → HCID 178474312, compound

HRID 133786Notes

Reaction equation

HRID 133786 reaction equation
[C:1]([NH:8][C:9](=[NH:12])SC)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN(C(C)C)C(C)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[NH2:35][CH2:36][C:37]1[CH:42]=[C:41]([Cl:43])[C:40]([NH:44][C:45](=[O:47])[CH3:46])=[C:39]([Cl:48])[CH:38]=1>C(Cl)Cl>[C:45]([NH:44][C:40]1[C:39]([Cl:48])=[CH:38][C:37]([CH2:36][NH:35]/[C:9](/[NH2:12])=[N:8]\[C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[CH:42][C:41]=1[Cl:43])(=[O:47])[CH3:46]

Participants

6

Reactant 4

HCID 9845Trifluoroacetic anhydrideHCID 81531DiisopropylethylamineHCID 58962993N-(4-(aminomethyl)-2,6-dichlorophenyl)acetamideHCID 137319820tert-butyl N-[(methylsulfanyl)methanimidoyl]carbamate

Product 1

HCID 178474312HCID 178474312, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of mono-N-Boc-S-methylisothiourea (Preparation C, 764 mg, 4.0 mmol) and DIPEA (3.0 mL) in CH2Cl2 (8.0 mL) was added trifluoroacetic anhydride (924 mg, 4.4 mmol). The mixture was stirred at rt for 30 min, and then N-(4-(aminomethyl)-2,6-dichlorophenyl)acetamide (930 mg, 4.0 mmol) was added. The resulting mixture was stirred at rt overnight. The solvent was removed. Then 15 mL of MeOH and K2CO3 (1.2 g) were added. After stirring at rt for 30 min, the MeOH was removed. 50 mL of HCl (1 N) was added, and the mixture was washed with Et2O (50 mL) and then neutralized with 50% NaOH to pH=12. The aqueous layer was then extracted with EtOAc (2×100 mL). The organic layer was dried and concentrated to give 1.1 g (yield 73%) of the title compound. MS (ESI) (M+H)+=375.06. 1H NMR (500 MHz, CD3OD) δ 7.39 (s, 2 H), 4.41 (s, 2 H), 2.19 (s, 3 H), 1.45 (s, 9 H).

Workup

  1. stirringThe resulting mixture was stirred at rt overnight
  2. customThe solvent was removed
  3. additionThen 15 mL of MeOH and K2CO3 (1.2 g) were added
  4. stirringAfter stirring at rt for 30 min
  5. customthe MeOH was removed
  6. addition50 mL of HCl (1 N) was added
  7. washthe mixture was washed with Et2O (50 mL)
  8. extractionThe aqueous layer was then extracted with EtOAc (2×100 mL)
  9. customThe organic layer was dried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-983ac844ccdb447e987706cb84a982f6
Source dataset
uspto-grants-2008_06
Patent number
US07390925B2

Reaction notes

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