4-chloro-N-{3-[(methylsulfonyl)methyl]phenyl}-1,3,5-triazin-2-amine → HCID 178434346, compound

HRID 855628Notes

Reaction equation

HRID 855628 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([NH2:11])=[CH:8][CH:9]=2)[NH:4][N:3]=1.[Cl:12][C:13]1[N:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:21]=2)[N:14]=1>C(O)(C)C>[ClH:12].[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:17]3[N:16]=[C:15]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][S:27]([CH3:30])(=[O:28])=[O:29])[CH:21]=4)[N:14]=[CH:13][N:18]=3)=[CH:8][CH:9]=2)[NH:4][N:3]=1

Participants

4

Reactant 2

HCID 219563434-chloro-N-{3-[(methylsulfonyl)methyl]phenyl}-1,3,5-triazin-2-amineHCID 178434350HCID 178434350, compound

Product 1

HCID 178434346HCID 178434346, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a flask containing a magnetic stir bar was added 0.03 g (0.20 mmol) of 3-methyl-1H-indazol-6-amine and 0.060 g (0.20 mmol) of 4-chloro-N-{3-[(methylsulfonyl)methyl]phenyl}-1,3,5-triazin-2-amine and 2 mL of isopropanol and the resultant mixture was heated at reflux for ca. 16 hours. Upon cooling the reaction mixture a solid precipitated. The solid was filtered and washed with ethyl acetate (2×4 mL), acetonitrile (4 mL), and ethyl ether (4 mL) and dried under vacuum to give N2-(3-methyl-1H-indazol-6-yl)-N4-{3-[(methylsulfonyl)methyl]phenyl}-1,3,5-triazine-2,4-diamine hydrochloride as a solid. The solid was purified by C-18 RP-HPLC using an acetonitrile/water gradient containing 0.5% trifluoroacetic acid buffer. Concentrating the proper fractions gave 0.015 g (10%) of N2-(3-methyl-1H-indazol-6-yl)-N4-{3-[(methylsulfonyl)methyl]phenyl}-1,3,5-triazine-2,4-diamine trifluoroacetate as a white solid. HNMR: δ12.4 (br s, 1H), 9.9 (br s, 1H), 8.34 (s, 1H), 7.8 (br s, 1H), 7.67 (br s, 1H), 7.56 (d, 1H), 7.29(m, 2H), 7.02 (d, 1H), 4.34 (br s, 2H), 2.83 (br s, 3H), 2.40 (s, 3H). MS (ES+, m/z)=409 (M+H).

Workup

  1. additionTo a flask containing a magnetic stir bar
  2. temperatureat reflux for ca. 16 hours
  3. temperatureUpon cooling the reaction mixture a solid
  4. customprecipitated
  5. filtrationThe solid was filtered
  6. washwashed with ethyl acetate (2×4 mL), acetonitrile (4 mL), and ethyl ether (4 mL)
  7. customdried under vacuum

Sources & evidence

ORD record
ord-8a151a3987e844dfb38f142c268f18df
Source dataset
uspto-grants-2007_08
Patent number
US07262203B2

Reaction notes

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