Morpholine → HCID 67116355, compound

HRID 244039Notes

Reaction equation

HRID 244039 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([N:14]2[CH2:21][CH:20]3[CH:16]([CH2:17][N:18]([C:22](=[O:35])[C:23]4[C:28]([N:29]5[N:33]=[CH:32][CH:31]=[N:30]5)=[CH:27][CH:26]=[CH:25][C:24]=4[F:34])[CH2:19]3)[CH2:15]2)[N:8]=1)(=O)=O.[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1>>[NH3:8].[F:34][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]([N:29]2[N:33]=[CH:32][CH:31]=[N:30]2)[C:23]=1[C:22]([N:18]1[CH2:17][CH:16]2[CH:20]([CH2:21][N:14]([C:9]3[N:10]=[C:11]([CH3:13])[CH:12]=[C:7]([N:38]4[CH2:43][CH2:42][O:41][CH2:40][CH2:39]4)[N:8]=3)[CH2:15]2)[CH2:19]1)=[O:35]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 86669176HCID 86669176, compound

Product 2

HCID 222AmmoniaYield 8%HCID 67116355HCID 67116355, compoundYield 78%

Procedure

A mixture of Intermediate 58 (137 mg, 0.254 mmol) and morpholine (1.3 mL) was stirred 14 h at room temperature. The mixture was concentrated in vacuo. Chromatography (DCM to 8% 2 M NH3 in MeOH/DCM) afforded the desired product as a pale yellow foam (95 mg, 78%). MS (ESI) mass calculated for C24H27FN8O2, 478.53; m/z found, 479.3. 1H NMR (500 MHz, CDCl3): 7.86-7.78 (m, 2H), 7.72 (s, 1H), 7.51-7.44 (m, 1H), 7.18-7.10 (m, 1H), 5.77-5.72 (m, 1H), 3.99-3.47 (m, 13H), 3.28-3.21 (m, 1H), 3.09-2.91 (m, 2H), 2.90-2.86 (m, 2H), 2.25 (s, 3H).

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-a0db7f35be924c5fb841a44249688797
Source dataset
uspto-grants-2014_02
Patent number
US08653263B2

Reaction notes

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