m-Chloroperbenzoic acid → HCID 58255094, compound

HRID 1897734Notes

Reaction equation

HRID 1897734 reaction equation
[Cl:1][C:2]1[C:3]([NH:25][C:26]2[CH:30]=[C:29]([CH3:31])[NH:28][N:27]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[C:13]([CH3:15])[C:12]([CH:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH3:23])[CH2:18][CH2:17]3)=[CH:11][C:10]=2[F:24])=[N:6][CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:40])C=1>C(Cl)Cl.CO>[Cl:1][C:2]1[C:3]([NH:25][C:26]2[CH:30]=[C:29]([CH3:31])[NH:28][N:27]=2)=[N:4][C:5]([NH:8][C:9]2[C:10]([F:24])=[CH:11][C:12]([CH:16]3[CH2:21][CH2:20][N+:19]([O-:40])([CH2:22][CH3:23])[CH2:18][CH2:17]3)=[C:13]([CH3:15])[CH:14]=2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 58254899HCID 58254899, compound

Product 1

HCID 58255094HCID 58255094, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloro-N2-(4-(1-ethylpiperidin-4-yl)-2-fluoro-5-methylphenyl)-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine (22.2 mg, 0.05 mmol) in DCM (10 mL) and MeOH (1 mL) was added MCPBA (11.2 mg, 0.07 mmol). The reaction was stirred at room temperature overnight. The reaction mixture was partitioned between DCM and saturated aqueous NaHCO3, the combined organic extracts were dried (Na2SO4), and concentrated in vacuo. The crude product was purified by RP-HPLC to afford 4-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-5-fluoro-2-methylphenyl)-1-ethylpiperidine-1-oxide; 1HNMR (MeOD-d4) δ7.91 (s, 1H), 7.69 (d, 1H), 7.00 (d, 1H), 6.15 (s, 1H), 3.28 (m, 4H), 2.91 (m, 1H), 2.32 (m, 2H), 2.20 (s, 3H), 2.16 (s, 3H), 1.83 (s, 2H), 1.64 (d, 2H), 1.31 (t, 3H); ESMS m/z 460.2 (M+H+).

Workup

  1. customThe reaction mixture was partitioned between DCM and saturated aqueous NaHCO3
  2. dry with materialthe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by RP-HPLC

Sources & evidence

ORD record
ord-b1dc3cd88d8b44669f005cd8e04e96d5
Source dataset
uspto-grants-2013_08
Patent number
US08519129B2

Reaction notes

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