Triethylamine → HCID 86760957, compound

HRID 730447Notes

Reaction equation

HRID 730447 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[N:7][C:8]([CH3:13])=[CH:9][C:10]=2[CH3:12])[N:5]([C@@H:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16][CH2:15]2)[C:4]=1/[CH:24]=[CH:25]/[C:26]([OH:28])=O)#[N:2].C(Cl)(=O)C(Cl)=O.[NH2:35][C:36]1[CH:41]=[CH:40][N:39]=[C:38]([Cl:42])[CH:37]=1.C(N(CC)CC)C>C1COCC1.O.CN(C=O)C>[Cl:42][C:38]1[CH:37]=[C:36]([NH:35][C:26](=[O:28])/[CH:25]=[CH:24]/[C:4]2[N:5]([C@@H:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17][CH2:16][CH2:15]3)[C:6]3=[N:7][C:8]([CH3:13])=[CH:9][C:10]([CH3:12])=[C:11]3[C:3]=2[C:1]#[N:2])[CH:41]=[CH:40][N:39]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 844322-Chloropyridin-4-amineHCID 69057218(2E)-3-{3-cyano-4,6-dimethyl-1-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl]prop-2-enoic acid

Product 1

HCID 86760957HCID 86760957, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2E)-3-{3-cyano-4,6-dimethyl-1-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl}prop-2-enoic acid (300 mg, 0.808 mmol) in THF (3 ml) were added DMF (0.03 ml) and oxalylchloride (0.0846 ml, 0.970 mmol), the mixture was stirred at room temperature for 1 hour and the solvent was distilled off under reduced pressure. The residue was added under ice-cooling to a solution of 4-amino-2-chloropyridine (209 mg, 1.62 mmol), triethylamine (0.451 ml, 3.24 mmol) and THF (3 ml), and the mixture was stirred under ice-cooling for 1 hour and at room temperature for 12 hours. The reaction solution was poured into water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane ethyl acetate=2:1) to give the objective product as a solid material.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionThe residue was added under ice-
  3. stirringthe mixture was stirred under ice-
  4. temperaturecooling for 1 hour and at room temperature for 12 hours
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane ethyl acetate=2:1)

Sources & evidence

ORD record
ord-566b07f425d148629825519ca0a9c9fb
Source dataset
uspto-grants-2009_09
Patent number
US07582651B2

Reaction notes

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