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

HRID 42352Notes

Reaction equation

HRID 42352 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:13][CH2:14][C:15]([F:18])([F:17])[F:16])[C:5]2[N:11]=[C:10](Cl)[CH:9]=[CH:8][C:6]=2[N:7]=1.[NH2:19][CH2:20][C:21]1[CH:22]=[C:23]([S:27]([NH2:30])(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=1.C(N([CH:37]([CH3:39])[CH3:38])CC)(C)C.CO.CN1C(=O)[CH2:46][CH2:45][CH2:44]1>O1CCOCC1.O>[CH3:23][S:27]([C:44]1[CH:45]=[C:46]([C:10]2[CH:9]=[CH:8][C:6]3[N:7]=[C:2]([NH:19][CH2:20][C:21]4[CH:22]=[C:23]([S:27]([NH2:30])(=[O:28])=[O:29])[CH:24]=[CH:25][CH:26]=4)[N:3]=[C:4]([NH:13][CH2:14][C:15]([F:18])([F:17])[F:16])[C:5]=3[N:11]=2)[CH:39]=[CH:37][CH:38]=1)(=[O:29])=[O:28]

Participants

8

Reactant 5

HCID 887MethanolHCID 13387N-methyl-2-pyrrolidoneHCID 81531Diisopropylethylamine3×HCID 167812603-(Aminomethyl)benzene-1-sulfonamide2×HCID 86653620(2,6-Dichloro-pyrido[3,2-d]pyrimidin-4-yl)-(2,2,2-trifluoro-ethyl)-amine

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

(2,6-Dichloro-pyrido[3,2-d]pyrimidin-4-yl)-(2,2,2-trifluoro-ethyl)-amine (2.3 g) and 3-Aminomethyl-benzenesulfonamide (0.336 g) were dissolved in NMP (10 mL) and dioxane (10 mL), treated with diisopropylethylamine (0.160 mL) and heated to reflux. After 8 h, additional portions of 3-Aminomethyl-benzenesulfonamide (440 mg) and diisopropylethylamine (0.200 mL). After an additional 12 h of heating, additional diisopropylethylamine was added (1.2 mL). The reaction mixture was stirred for another 24 h at reflux. Methanol (30 mL) was added followed by water (80 mL) and the mixture was allowed to cool to ambient temperature. A precipitate was collected and washed with 10% MeOH:water, and dried to give 1.2 g of the desired product which was used without further purification.

Workup

  1. temperatureheated to reflux
  2. temperatureAfter an additional 12 h of heating
  3. temperatureat reflux
  4. customA precipitate was collected
  5. washwashed with 10% MeOH
  6. dry with materialwater, and dried

Sources & evidence

ORD record
ord-3fa15e5d85f44e67b6115ed0fe4f3f02
Source dataset
uspto-grants-2013_09
Patent number
US08536187B2

Reaction notes

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