Ammonia → HCID 49798413, compound

HRID 908405Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH2:28])=[N:12][CH:13]=[C:14]([C:16]2[CH:17]=[N:18][N:19]([CH2:21][CH2:22][O:23]C(C)(C)C)[CH:20]=2)[CH:15]=1.N>C(O)(C(F)(F)F)=O.CO>[NH2:28][C:11]1[N:12]=[CH:13][C:14]([C:16]2[CH:17]=[N:18][N:19]([CH2:21][CH2:22][OH:23])[CH:20]=2)=[CH:15][C:10]=1[C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

3-(1,3-benzoxazol-2-yl)-5-[1-(2-tert-butoxyethyl)pyrazol-4-yl]pyridin-2-amine (485 mg) was dissolved in TFA (3 ml). The resulting solution was stirred at 25° C. for 1 hour. A solution 7N of ammonia in methanol (20 ml) was added to the mixture and adsorbed on silica gel. The crude product was purified by flash chromatography on silica gel eluting with 1 to 5% methanolic ammonia (7 N) in dichloromethane. The solvent was evaporated to dryness to afford 2-[4-[6-amino-5-(1,3-benzoxazol-2-yl)-3-pyridyl]pyrazol-1-yl]ethanol (315 mg). NMR Spectrum: (DMSOd6) 3.75-3.81 (m, 2H), 4.17 (t, 2H), 4.94 (t, 1H), 7.40-7.49 (m, 2H), 7.64 (bs, 2H), 7.79-7.82 (m, 1H), 7.83-7.86 (m, 1H), 7.92 (s, 1H), 8.21 (s, 1H), 8.41 (d, 1H), 8.52 (d, 1H); Mass spectrum: M+H+ 322.

Workup

customThe crude product was purified by flash chromatography on silica gel eluting with 1 to 5% methanolic ammonia (7 N) in dichloromethane
customThe solvent was evaporated to dryness

Sources & evidence

ORD record: ord-64b7c476483b4924a18243fe2906c97b
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017611B2

Reaction notes

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