m-Chloroperbenzoic acid → 3-(1,3-Benzoxazol-2-yl)-5-[1-(1-methyl-1-oxido-piperidin-1-ium-4-yl)pyrazol-4-yl]pyridin-2-amine

HRID 908375Notes

Reaction equation

HRID 908375 reaction equation
ClC1C=C(C(OO)=[O:9])C=CC=1.[O:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[C:21]1[C:22]([NH2:39])=[N:23][CH:24]=[C:25]([C:27]2[CH:28]=[N:29][N:30]([CH:32]3[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]3)[CH:31]=2)[CH:26]=1>C(Cl)Cl>[O:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[C:21]1[C:22]([NH2:39])=[N:23][CH:24]=[C:25]([C:27]2[CH:28]=[N:29][N:30]([CH:32]3[CH2:33][CH2:34][N+:35]([CH3:38])([O-:9])[CH2:36][CH2:37]3)[CH:31]=2)[CH:26]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 425993593-(1,3-Benzoxazol-2-yl)-5-[1-(1-methyl-4-piperidyl)pyrazol-4-yl]pyridin-2-amine

Product 1

HCID 866301463-(1,3-Benzoxazol-2-yl)-5-[1-(1-methyl-1-oxido-piperidin-1-ium-4-yl)pyrazol-4-yl]pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chlorobenzenecarboperoxoic acid (0.046 g) was added to 3-(1,3-benzoxazol-2-yl)-5-[1-(1-methyl-4-piperidyl)pyrazol-4-yl]pyridin-2-amine (0.100 g) in DCM (10 ml). The resulting solution was stirred for 5 minutes. The resultant precipitate was collected by filtration, washed with DCM (2 ml) and dried under vacuum. The residue was purified by SCX ion exchange chromatography (elution with 7M methanolic ammonia) and there was thus obtained 3-(1,3-benzoxazol-2-yl)-5-[1-(1-methyl-1-oxido-piperidin-1-ium-4-yl)pyrazol-4-yl]pyridin-2-amine (0.026 g); Mass Spectrum: M+H+ 391.29; RT 1.18 min; NMR Spectrum: (DMSOd6) 8.49 (d, 1H), 8.41 (d, 1H), 8.32 (s, 1H), 7.88 (s, 1H), 7.78 (dd, 1H), 7.73 (dd, 1H), 7.57 (br s, 2H), 7.38 (m, 2H), 4.26 (tt, 1H), 3.46 (m, 2H), 3.11 (s, 3H), 3.06 (m, 2H), 2.68 (m, 2H), 1.90 (br m, 2H).

Workup

  1. filtrationThe resultant precipitate was collected by filtration
  2. washwashed with DCM (2 ml)
  3. customdried under vacuum
  4. customThe residue was purified by SCX ion exchange chromatography (elution with 7M methanolic ammonia) and there
  5. customRT 1.18 min

Sources & evidence

ORD record
ord-3c94da2a089d476ca493392fe87662ff
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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