Potassium Carbonate → 3-{[6-(3-Methanesulfonyl-phenyl)-4-(2,2,2-trifluoro-ethylamino)-pyrido[3,2-d]pyrimidin-2-ylamino]-methyl}-benzenesulfonamide

HRID 42353Notes

Reaction equation

HRID 42353 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]=[C:7]([NH:18][CH2:19][C:20]3[CH:21]=[C:22]([S:26]([NH2:29])(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=3)[N:8]=[C:9]([NH:12][CH2:13][C:14]([F:17])([F:16])[F:15])[C:10]=2[N:11]=1.[CH3:30][S:31]([C:34]1[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][CH:39]=1)(=[O:33])=[O:32].C(=O)([O-])[O-].[K+].[K+]>COCCOC.O>[CH3:30][S:31]([C:34]1[CH:39]=[C:38]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]=[C:7]([NH:18][CH2:19][C:20]4[CH:21]=[C:22]([S:26]([NH2:29])(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=4)[N:8]=[C:9]([NH:12][CH2:13][C:14]([F:17])([F:15])[F:16])[C:10]=3[N:11]=2)[CH:37]=[CH:36][CH:35]=1)(=[O:33])=[O:32]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 866536213-{[6-Chloro-4-(2,2,2-trifluoro-ethylamino)-pyrido[3,2-d]pyrimidin-2-ylamino]-methyl}-benzenesulfonamide

Product 1

HCID 446227053-{[6-(3-Methanesulfonyl-phenyl)-4-(2,2,2-trifluoro-ethylamino)-pyrido[3,2-d]pyrimidin-2-ylamino]-methyl}-benzenesulfonamideYield 49.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

3-{[6-Chloro-4-(2,2,2-trifluoro-ethylamino)-pyrido[3,2-d]pyrimidin-2-ylamino]-methyl}-benzenesulfonamide (0.077 g) was combined with 3-methylsulfonyl-phenylboronic acid (0.067 g), palladium tetrakistriphenylphosphine (0.006 g) and potassium carbonate (0.121 g). The mixture was suspended in DME (1.6 mL) and water (0.8 mL), sealed and heated by microwave to 120° C. for 3 min. Crude product was precipitated by the addition of water. The precipitate was filtered and purified by reverse phase HPLC (5-100% ACN/H2O+0.1% TFA) to give 0.048 g (41% yield) of the title compound, which was characterized by its NMR and mass spectrum as follows: 1H NMR (d6-DMSO): d 3.34 (s, 3H), 4.40-4.46 (m, 2H), 4.73-4.82 (m, 2H), 7.35 (s, 2H), 7.52-7.7.64 (m, 2H), 7.73-7.75 (m, 1H), 7.83-7.87 (m, 2H), 8.03-8.06 (m, 2H), 8.58-8.62 (m, 1H), 8.68 (s, 1H), 8.80 (d, 1H), 9.10 (bs, 1H), 9.98 (bs, 1H); MS (m/z): 567.1 ([M+H]+, 100).

Workup

  1. customCrude product was precipitated by the addition of water
  2. filtrationThe precipitate was filtered
  3. custompurified by reverse phase HPLC (5-100% ACN/H2O+0.1% TFA)

Sources & evidence

ORD record
ord-8728a82239b14e958fadd378bbf5c11e
Source dataset
uspto-grants-2013_09
Patent number
US08536187B2

Reaction notes

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