Trifluoroacetic acid → HCID 178434779, compound

Temperature

50 °C

To PS-carbodiimide resin (Argonaut Technologies) (1.069 g, 1.71 mmol, 1.6 mmol/g) placed in a 20 mL vial was added anhydrous 1,2-dichloroethane (6.0 mL), N,N′-bis(tert-butoxycarbonyl)thiourea (235 mg, 0.85 mmol) in anhydrous 1,2-dichloroethane (2.0 mL), and 5-amino-3,4-dimethylisoxazole (63.9 mg, 0.57 mmol) solution or dispersion in anhydrous 1,2-dichloroethane (1.0 mL). The reaction mixture was shaken at 50° C. until the reaction completed, typically for 36 hours. The reaction mixture was brought to room temperature and PS-trisamine (317 mg, 1.14 mmol, 3.6 mmol/g) was added. The reaction mixture was shaken at room temperature for 24 hours. The resin was removed by filtration and washed with 1,2-dichloroethane (3.0 mL) and methanol (3.0 mL). The combined organic layers were dried in a Genevac at 40° C. The resultant crude reaction mixture was mixed with TFA in dichloromethane (25% vol., 5.0 mL) and shaken at room temperature for 6 hours followed by evaporation in Genevac 40° C. to give crude xxix-187 (152 mg, 99%).: MS m/z═155 (M+H).

1. customwas brought to room temperature
2. stirringThe reaction mixture was shaken at room temperature for 24 hours
3. customThe resin was removed by filtration
4. washwashed with 1,2-dichloroethane (3.0 mL) and methanol (3.0 mL)
5. customThe combined organic layers were dried in a Genevac at 40° C
6. customThe resultant crude reaction mixture
7. stirring5.0 mL) and shaken at room temperature for 6 hours
8. customfollowed by evaporation in Genevac 40° C.
9. customto give crude xxix-187 (152 mg, 99%)

ORD record

ord-542dd7f2aece44aaad43f853eeba987d

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07459448B2