Pyridine → HCID 19920060, compound

HRID 1648493Notes

Reaction equation

HRID 1648493 reaction equation
[N:1]1([C:6]2[N:11]=[C:10]([N:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)[CH:9]=[C:8]([N:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][O:26][C:27]4[CH:35]=[CH:34][CH:33]=[C:32]5[C:28]=4[CH:29]=[C:30]([C:36]([NH2:38])=O)[NH:31]5)[CH2:19][CH2:18]3)[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCOCC1.C(Cl)Cl>[C:36]([C:30]1[NH:31][C:32]2[C:28]([CH:29]=1)=[C:27]([O:26][CH2:25][CH2:24][CH2:23][N:20]1[CH2:21][CH2:22][N:17]([C:8]3[N:7]=[C:6]([N:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[N:11]=[C:10]([N:12]4[CH2:16][CH2:15][CH2:14][CH2:13]4)[CH:9]=3)[CH2:18][CH2:19]1)[CH:35]=[CH:34][CH:33]=2)#[N:38]

Participants

6

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydride2×HCID 15293733HCID 15293733, compound

Product 1

HCID 19920060HCID 19920060, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent3×

Procedure

A solution of 4-[3-[4-[2,4-dipyrrolidino-6-pyrimidinyl]-1-piperazinyl]propoxy]indole-2-carboxamide (0.45 g) in dioxane (12 ml), under nitrogen, is mixed with pyridine (0.33 ml), cooled to 12° and treated during 5 min. with a solution of trifluoroacetic anhydride (0.31 ml) in dioxane (2.5 ml). The mixture is stirred at 12° for 15 min. and at 20°-25° for 18 hr. It is again cooled to 12° and treated with additional trifluoroacetic anhydride (0.1 ml) in dioxane (1 ml). The mixture is kept at 12° for 15 min. and at 20°-25° for 4 hr. It is then diluted with methylene chloride; washed with saturated sodium bicarbonate, water and saline, dried over magnesium sulfate and concentrated under reduced pressure. The residue is chromatographed over silica gel (275 ml) with eluting with ammonium hydroxide/methanol/methylene chloride (0.5/5/94.5). The product isolated from this column is crystallized from methanol to give the title compound, mp of an analytical sample 147°-149°;, Anal. calc'd for C28H36N8O: C, 67.17; H, 7.25; N, 22.38. Found: C, 66.80; H, 7.34; N, 21.78. ##STR7##

Workup

  1. temperaturecooled to 12°
  2. temperatureIt is again cooled to 12°
  3. waitThe mixture is kept at 12° for 15 min. and at 20°-25° for 4 hr
  4. washwashed with saturated sodium bicarbonate, water and saline
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is chromatographed over silica gel (275 ml)
  8. washwith eluting with ammonium hydroxide/methanol/methylene chloride (0.5/5/94.5)
  9. customThe product isolated from this column
  10. customis crystallized from methanol

Sources & evidence

ORD record
ord-df40986e300d46678f8d3701de6f47f5
Source dataset
uspto-grants-1995_07
Patent number
US05436337

Reaction notes

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