Pyridine → HCID 86710188, compound

HRID 2284425Notes

Reaction equation

HRID 2284425 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:17]=[N:16][C:15]3[C:14]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[N:13][C:12]([C:24]4[CH:25]=[N:26][C:27]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[N:28][CH:29]=4)=[N:11][C:10]=3[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[F:44][C:45]1[CH:50]=[CH:49][C:48]([S:51](Cl)(=[O:53])=[O:52])=[CH:47][CH:46]=1>CO.C(Cl)(Cl)Cl>[F:44][C:45]1[CH:50]=[CH:49][C:48]([S:51]([NH:1][C:2]2[CH:3]=[C:4]([C:8]3[CH:17]=[N:16][C:15]4[C:14]([N:18]5[CH2:23][CH2:22][O:21][CH2:20][CH2:19]5)=[N:13][C:12]([C:24]5[CH:25]=[N:26][C:27]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:34])([CH3:36])[CH3:35])=[N:28][CH:29]=5)=[N:11][C:10]=4[CH:9]=3)[CH:5]=[CH:6][CH:7]=2)(=[O:53])=[O:52])=[CH:47][CH:46]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 86710176HCID 86710176, compound

Product 1

HCID 86710188HCID 86710188, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a 25 mL flask, tert-butyl (5-(7-(3-aminophenyl)-4-morpholinopyrido[3,2-d]pyrimidin-2-yl)pyrimidin-2-yl)carbamate (Example 7, Step 2) (0.1 g, 0.0002 mol) and pyridine (4 mL) were added. To the same flask, 4-fluorobenzenesulfonyl chloride (0.038 g, 0.0002 mol) was added. The reaction mixture was stirred at room temperature for 12 hours. The reaction mixture was diluted with 10% methanol in chloroform and washed with water. The organic layer was washed with brine, dried over sodium sulfate and was evaporated to provide the crude product. The crude product was purified by flash column chromatography (3% methanol in chloroform) to obtain the title compound (0.06 g, 45%). 1H NMR (300 MHz, DMSO-d6): δ 10.57 (s, 1H), 10.42 (s, 1H), 9.48 (s, 1H), 8.98 (d, J=2.1 Hz, 1H), 8.23 (d, J=2.1 Hz, 1H), 7.91 (dd, J′=5.1 Hz, J″=3.9 Hz, 2H), 7.65 (d, J=7.8 Hz, 1H), 7.56 (s, 1H), 7.45 (dd, J′=8.7 Hz, J″=1.5 Hz, 3H), 7.23 (d, J=7.8 Hz, 1H), 4.57 (br s, 4H), 3.83 (br s, 4H), 1.49 (s, 9H). LC-MS (ESI): Calculated mass: 658.2; Observed mass [M+H]+: 658.9 (RT=1.69 min).

Workup

  1. washwashed with water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customwas evaporated
  5. customto provide the crude product
  6. customThe crude product was purified by flash column chromatography (3% methanol in chloroform)

Sources & evidence

ORD record
ord-5ebc61c52a034e2fbaf768c80c2fb940
Source dataset
uspto-grants-2015_09
Patent number
US09145411B2

Reaction notes

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