4-chloro-N-{3-[(methylsulfonyl)methyl]phenyl}-1,3,5-triazin-2-amine → N2-methyl-N2-(3-methyl-1H-indazol-6-yl)-N4-{3-[(methylsulfonyl) methyl]phenyl}-1,3,5-triazine-2,4-diamine hydrochloride

HRID 855629Notes

Reaction equation

HRID 855629 reaction equation
[CH3:1][NH:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:12])=[N:8][NH:9]2)=[CH:5][CH:4]=1.[Cl:13][C:14]1[N:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH:22]=2)[N:15]=1>C(O)(C)C>[ClH:13].[CH3:1][N:2]([C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:12])=[N:8][NH:9]2)=[CH:5][CH:4]=1)[C:18]1[N:17]=[C:16]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][S:28]([CH3:31])(=[O:29])=[O:30])[CH:22]=2)[N:15]=[CH:14][N:19]=1

Participants

4

Reactant 2

HCID 219563434-chloro-N-{3-[(methylsulfonyl)methyl]phenyl}-1,3,5-triazin-2-amineHCID 21956372N,3-dimethyl-1H-indazol-6-amine

Product 1

HCID 178434349N2-methyl-N2-(3-methyl-1H-indazol-6-yl)-N4-{3-[(methylsulfonyl) methyl]phenyl}-1,3,5-triazine-2,4-diamine hydrochlorideYield 42%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a flask containing a magnetic stir bar was added 0.027 g (0.17 mmol) of N,3-dimethyl-1H-indazol-6-amine and 0.058 g (0.19 mmol) of 4-chloro-N-{3-[(methylsulfonyl)methyl]phenyl}-1,3,5-triazin-2-amine and 2 mL of isopropanol and the resultant mixture 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 0.03 g (42%) of N2-methyl-N2-(3-methyl-1H-indazol-6-yl)-N4-{3-[(methylsulfonyl) methyl]phenyl}-1,3,5-triazine-2,4-diamine hydrochloride as a light pink solid. Some of the peaks in the NMR spectrum are broad at room temperature. Heating to 90° C. produces peaks that are well resolved. HNMR: δ12.5 (br s, 1H), 9.9 (br s, 1H), 8.24 (m, 1H) 7.72 (d, 1H) 7.5 (m), 7.38 (s, 1H), 7.01 (d, 1H) 6.9 (br s, 1H) 3.47 (s, 3H), 2.75 (br s, 3H), 2.47 (S, 3H). HNMR (at 90° C.): δ 9.62 (s, 1H), 8.29 (s, 1H), 7.76 (d, 1H), 7.66 (s, 1H), 7.54 (d, 1H), 7.43 (s, 1H) 7.1 (m, 3H), 4.13 (s, 2H), 3.56 (s, 3H), 2.93 (s, 3H), 2.55 (s, 3H); MS (ES+, m/z)=424 (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-59897b59cf244a5fb875156ede054608
Source dataset
uspto-grants-2007_08
Patent number
US07262203B2

Reaction notes

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