Water → HCID 22291610, compound

HRID 968111Notes

Reaction equation

HRID 968111 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([NH:10][C:11]2[CH:33]=[CH:32][C:14]3[CH2:15][CH2:16][C:17]4[C:18]([C:29]([NH2:31])=[O:30])=[N:19][N:20]([C:22]5[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=5)[C:21]=4[C:13]=3[CH:12]=2)=[O:9])=[C:4]([CH3:34])[CH:3]=1.[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1.O>CN(C)C(=O)C>[F:28][C:25]1[CH:26]=[CH:27][C:22]([N:20]2[C:21]3[C:13]4[CH:12]=[C:11]([NH:10][C:8]([C:5]5[CH:6]=[N:7][C:2]([N:35]6[CH2:40][CH2:39][O:38][CH2:37][CH2:36]6)=[CH:3][C:4]=5[CH3:34])=[O:9])[CH:33]=[CH:32][C:14]=4[CH2:15][CH2:16][C:17]=3[C:18]([C:29]([NH2:31])=[O:30])=[N:19]2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 22291445HCID 22291445, compound

Product 1

HCID 22291610HCID 22291610, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

The title compound of Example 246 (1.47 mmoles) and morpholine (23.1 mmoles) were dissolved in 10 mL of N,N-dimethylacetamide. The reaction mixture was then placed under nitrogen and stirred in an oil bath at 100° C. for 27 h. The mixture was partially stripped of solvent then added to water, filtered, and washed with water. The solid was recrystallized from acetonitrile, then dissolved in acetonitrile and dried over anhydrous MgSO4. The solvent was then stripped down to a solid. Mp: 301° C. (decomp.) 1H NMR (d6-DMSO, 400 MHz): δ 2.22 (s, 3H); 2.80-2.94 (m, 4H); 3.46 (t, 4H, J=4.8 Hz); 3.62 (t, 4H, J=4.8 Hz); 6.67 (s, 1H); 7.22-7.27 (m, 3H); 7.31-7.38 (m, 2H); 7.42 (dd, 1H, J=1.9 Hz, 8.2 Hz); 7.49-7.57 (m, 3H); 8.11 (s, 1H); 9.92 (s, 1H). 13C NMR (d6-DMSO, 100 MHz): δ 20.35, 20.38, 29.63, 45.55, 66.54, 108.46, 114.91, 117.02, 117.25, 119.91, 121.23, 122.78, 126.42, 128.64, 128.73, 129.36, 132.60, 136.82, 136.85, 138.38, 139.82, 143.15, 147.70, 148.03, 160.04, 161.39, 163.84, 164.47, 166.18. M+1=527

Workup

  1. filtrationfiltered
  2. washwashed with water
  3. customThe solid was recrystallized from acetonitrile
  4. dissolutiondissolved in acetonitrile
  5. dry with materialdried over anhydrous MgSO4

Sources & evidence

ORD record
ord-3bf32bffc30140bebe1c802fa990437f
Source dataset
uspto-grants-2005_10
Patent number
US06956052B2

Reaction notes

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