4-Aminotetrahydropyran → HCID 24794485, compound

HRID 2251078Notes

Reaction equation

HRID 2251078 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:13]2[N:14]=[C:15](S(C)(=O)=O)[N:16]=[CH:17][C:12]=2[CH:11]=[C:10]1[C:22]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=[O:23].[NH2:31][CH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>CN1CCCC1=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:13]2[N:14]=[C:15]([NH:31][CH:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[N:16]=[CH:17][C:12]=2[CH:11]=[C:10]1[C:22]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=[O:23]

Participants

4

Reactant 2

HCID 4192234-AminotetrahydropyranHCID 69217838HCID 69217838, compound

Product 1

HCID 24794485HCID 24794485, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of [7-(2,6-difluoro-phenyl)-2-methanesulfonyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-(4-fluoro-phenyl)-methanone, 4, (0.50 g, 1.28 mmol) in 1-methyl-2-pyrrolidinone (4 mL) is added 4-aminotetrahydropyran (0.18 g, 1.80 mmol). The reaction mixture is heated to 90° C. for 19 hours after which the reaction is cooled to room temperature and concentrated in vacuo. The crude residue is purified over silica (40% EtOAc/hexanes) to afford 444 mg of the desired product as a yellow solid: 1H NMR (300 MHz, CDCl3) δ 8.74 (s, 1H), 7.93 (dd, J=9.0, 5.4 Hz, 2H), 7.48-7.39 (m, 1H), 7.20 (t, J=9.0 Hz, 2H), 7.12-7.06 (m, 3H), 4.10-3.95 (m, 3H), 3.49 (t, J=7.6 Hz, 2H), 2.40 (t, J=7.6 Hz, 2H), 2.06-2.01 (m, 2H); HRMS calcd for C24H19F3N4O2 (M+H)+ 453.1539; found 453.1551.

Workup

  1. temperatureis cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe crude residue is purified over silica (40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-89c16dc427ff4332824e1deeda3883fb
Source dataset
uspto-grants-2008_01
Patent number
US07319102B1

Reaction notes

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