Triethylamine → HCID 19367096, compound

HRID 1416283Notes

Reaction equation

HRID 1416283 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11]Cl)[N:10]=2)[CH:7]=1.[F:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[C:17]#[N:18].C(N(CC)CC)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][N:25]3[CH2:24][CH2:23][N:22]([C:21]4[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][C:14]=4[F:13])[CH2:27][CH2:26]3)[N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5961133-Fluoro-4-piperazin-1-yl-benzonitrileHCID 48683896-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridine

Product 1

HCID 19367096HCID 19367096, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
77.5 °C

Procedure

A mixture of 6-chloro-2-(chloromethyl)imidazo[1,2-α]pyridine (Example 4, step 1, 0.857 g), 3-fluoro-4-(piperazin-1-yl)benzonitrile (1.039 g), triethylamine (0.75 mL), and THF (6 mL) is stirred for 3 h at 75-80° C. The mixture is then concentrated under reduced pressure and the residue is partitioned between dichloromethane and saturated sodium bicarbonate. The combined organic layers are dried with MgSO4 and concentrated under reduced pressure. The residue is chromatographed on silica gel using methanol/dichloromethane (4/96). The appropriate fractions are combined and concentrated. Ethyl ether is added to the residue and the resulting solid is collected, washed with additional ethyl ether, and dried under reduced pressure to give 1.25 g of the title compound. A portion of this material is recrystallized from ethyl acetate; mp 132-133° C. ; IR (mineral oil) 1255, 1513, 1246, 801, 1504 cm-1 ; 1H NMR (CDCl3) δ2.74, 3.26, 3.77, 6.90, 7.13, 7.25, 7.34, 7.53, 8.13.

Workup

  1. concentrationThe mixture is then concentrated under reduced pressure
  2. customthe residue is partitioned between dichloromethane and saturated sodium bicarbonate
  3. dry with materialThe combined organic layers are dried with MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is chromatographed on silica gel
  6. concentrationconcentrated
  7. additionEthyl ether is added to the residue
  8. customthe resulting solid is collected
  9. washwashed with additional ethyl ether
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-b78ad2b961354804a76e4241dd8ddb95
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

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