Ammonia → HCID 57687117, compound

HRID 908410Notes

Reaction equation

HRID 908410 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)[CH:12]=2)=[CH:4][C:3]=1[C:28]1[O:29][C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[N:32]=1.N>C(O)(C(F)(F)F)=O.CO>[O:29]1[C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[N:32]=[C:28]1[C:3]1[C:2]([NH2:1])=[N:7][CH:6]=[C:5]([C:8]2[CH:9]=[N:10][N:11]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[CH:12]=2)[CH:4]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 67388151HCID 67388151, compound

Product 1

HCID 57687117HCID 57687117, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 4-[2-[4-[6-amino-5-(1,3-benzoxazol-2-yl)-3-pyridyl]pyrazol-1-yl]ethyl]piperazine-1-carboxylate (90 mg) in TFA (3 ml) was stirred at 25° C. for 1 hour. A solution 7N 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 2 to 8% methanolic ammonia (7 N) in dichloromethane. The solvent was evaporated to dryness to afford 3-(1,3-benzoxazol-2-yl)-5-[1-(2-piperazin-1-ylethyl)pyrazol-4-yl]pyridin-2-amine (49.0 mg). NMR Spectrum: (DMSOd6) 2.29-2.42 (m, 4H), 2.64-2.70 (m, 4H), 2.71 (t, 2H), 4.23 (t, 2H), 7.41-7.49 (m, 2H), 7.65 (bs, 2H), 7.77-7.82 (m, 1H), 7.82-7.87 (m, 1H), 7.90 (s, 1H), 8.24 (s, 1H), 8.40 (d, 1H), 8.51 (d, 1H); Mass spectrum: M+H+ 390.

Workup

  1. customThe crude product was purified by flash chromatography on silica gel eluting with 2 to 8% methanolic ammonia (7 N) in dichloromethane
  2. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-f21858f762b34b2bb55a37934dab0e7e
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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