Hydrochloric Acid → HCID 44256443, compound

HRID 908404Notes

Reaction equation

HRID 908404 reaction equation
Cl.[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[C:11]1[C:12]([NH2:28])=[N:13][CH:14]=[C:15]([C:17]2[CH:18]=[N:19][N:20](C3CCCCO3)[CH:21]=2)[CH:16]=1.[CH2:29]([OH:31])[CH3:30]>>[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[C:11]1[C:12]([NH2:28])=[N:13][CH:14]=[C:15]([C:17]2[CH:18]=[N:19][N:20]([CH2:11][CH2:3][N:4]3[CH2:5][CH2:6][O:31][CH2:29][CH2:30]3)[CH:21]=2)[CH:16]=1.[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[C:11]1[C:12]([NH2:28])=[N:13][CH:14]=[C:15]([C:17]2[CH:21]=[N:20][NH:19][CH:18]=2)[CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 67389020HCID 67389020, compound

Product 2

HCID 44256443HCID 44256443, compoundHCID 57687026HCID 57687026, compound

Conditions

Temperature
25 °C

Procedure

The 3-(1,3-benzoxazol-2-yl)-5-(1H-pyrazol-4-yl)pyridin-2-amine was prepared as follows: Hydrogen chloride (16.26 ml, 4N in dioxane) was added to a stirred suspension 3-(1,3-benzoxazol-2-yl)-5-(1-tetrahydropyran-2-ylpyrazol-4-yl)pyridin-2-amine (4.7 g) dissolved in ethanol (30 ml). The resulting mixture was stirred at 25° C. for 2 hours. The reaction was evaporated under reduce pressure, adsorbed on silica gel and purified by flash chromatography on silica gel eluting with 20 to 80% methanolic ammonia (7 N) in dichloromethane. The solvent was evaporated to dryness to afford 3-(1,3-benzoxazol-2-yl)-5-(1H-pyrazol-4-yl)pyridin-2-amine (3.35 g). NMR Spectrum: (CDCl3) 7.39-7.50 (m, 2H), 7.65 (bs, 2H), 7.80 (dd, 1H), 7.84 (dd, 1H), 7.98 (bs, 1H), 8.24 (bs, 1H), 8.45 (d, 1H), 8.55 (d, 1H); Mass spectrum: M+H+ 278

Workup

  1. customThe reaction was evaporated
  2. custompurified by flash chromatography on silica gel eluting with 20 to 80% methanolic ammonia (7 N) in dichloromethane
  3. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-ff1922f85d884a7fa53b23a71332cf14
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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