HCID 45103348, compound → HCID 67388613, compound

HRID 908431Notes

Reaction equation

HRID 908431 reaction equation
COC1C=C(OC)C=CC=1C[O:12][C:13]1[C:18]2[N:19]=[C:20]([C:22]3[C:23]([NH2:28])=[N:24][CH:25]=[CH:26][CH:27]=3)[O:21][C:17]=2[CH:16]=[CH:15][CH:14]=1>C(O)(C(F)(F)F)=O>[NH2:28][C:23]1[C:22]([C:20]2[O:21][C:17]3[C:18](=[C:13]([OH:12])[CH:14]=[CH:15][CH:16]=3)[N:19]=2)=[CH:27][CH:26]=[CH:25][N:24]=1

Participants

3

Reactant 1

HCID 45103348HCID 45103348, compound

Product 1

HCID 67388613HCID 67388613, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
25 °C

Procedure

TFA (10 ml) was added to 3-[4-[(2,4-dimethoxyphenyl)methoxy]-1,3-benzoxazol-2-yl]pyridin-2-amine (1.4 g). The resulting solution was stirred at 25° C. for 2 hours. The TFA was evaporated under reduced pressure. Toluene was added and the mixture was evaporated. The solid was triturated with water. The pH was adjusted to 7 with a 30% solution of ammonia. The solid was filtered and washed with water, diethyl ether and dried under reduced pressure to afford 2-(2-amino-3-pyridyl)-1,3-benzoxazol-4-ol (617 mg) as a solid. NMR Spectrum: (DMSOd6): 6.74-6.83 (m, 2H), 7.18 (d, 1H), 7.23 (dd, 1H), 7.84 (bs, 2H), 8.20 (d, 1H), 8.26 (d, 1H), 10.43 (s, 1H); Mass spectrum: M+H+ 228

Workup

  1. customThe TFA was evaporated under reduced pressure
  2. additionToluene was added
  3. customthe mixture was evaporated
  4. customThe solid was triturated with water
  5. filtrationThe solid was filtered
  6. washwashed with water, diethyl ether
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-61cfccf8dc9948be835203fa6e540ed6
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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