Triethylamine → HCID 22291566, compound

HRID 968113Notes

Reaction equation

HRID 968113 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]2[CH2:6][CH2:7][C:8]3[C:9]([C:20]([NH2:22])=[O:21])=[N:10][N:11]([C:13]4[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=4)[C:12]=3[C:4]=2[CH:3]=1.[Cl:25][C:26]1[C:31]([C:32](O)=[O:33])=[CH:30][C:29]([N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)=[N:28][CH:27]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.O>[Cl:25][C:26]1[C:31]([C:32]([NH:1][C:2]2[CH:24]=[CH:23][C:5]3[CH2:6][CH2:7][C:8]4[C:9]([C:20]([NH2:22])=[O:21])=[N:10][N:11]([C:13]5[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=5)[C:12]=4[C:4]=3[CH:3]=2)=[O:33])=[CH:30][C:29]([N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)=[N:28][CH:27]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22291707HCID 22291707, compoundHCID 22291910HCID 22291910, compound

Product 1

HCID 22291566HCID 22291566, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

The title compound of Example 244 (0.757 mmoles), 5-chloro-2-morpholin-4-ylisonicotinic acid, (1.38 mmoles), and HATU (1.57 mmoles) were dissolved in 5 mL DMF followed by the addition of 0.4 mL of triethylamine. The mixture was stirred at room temperature for 3 hrs and partially stripped of DMF. The reaction mixture was then added to water, filtered, and washed with water. The solid was dissolved in THF, decolorized with decolorizing carbon, and dried over anhydrous MgSO4. The THF was stripped and the solid triturated in diethyl ether three times, then triturated in ethanol, and twice more with acetonitrile, filtered and dried under vacuum. Mp: 309-313° C. 1H NMR (d6-DMSO, 400 MHz): δ 2.80-2.95 (m, 4H); 3.42 (t, 4H, J=5 Hz); 3.62 (t, 4H, J=5 Hz); 6.88 (s, 1H); 7.17-7.21 (m, 1H); 7.23-7.41 (m, 5H); 7.49-7.58 (m, 3H); 8.14 (s, 1H); 10.31 (s, 1H). 13C NMR (d6-DSMO, 100 MHz): δ 20.34, 29.70, 45.74, 66.50, 106.55, 114.97, 115.87, 117.09, 117.32, 120.05, 121.41, 126.67, 128.64, 128.73, 129.62, 133.47, 136.80, 136.82, 137.48, 139.64, 143.21, 145.28, 147.54, 158.30, 161.39, 163.85, 164.45. M+1=547.

Workup

  1. filtrationfiltered
  2. washwashed with water
  3. dissolutionThe solid was dissolved in THF
  4. dry with materialdried over anhydrous MgSO4
  5. customthe solid triturated in diethyl ether three times
  6. customtriturated in ethanol
  7. filtrationtwice more with acetonitrile, filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-8753133f70ad4a00875f41eff630eddf
Source dataset
uspto-grants-2005_10
Patent number
US06956052B2

Reaction notes

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