Triethylamine → HCID 178425225, compound

HRID 2206492Notes

Reaction equation

HRID 2206492 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11](O)=[O:12])=[C:9]([CH3:14])[N:8]([C@@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])[C:6]=2[N:7]=1.ON1C2C=CC=CC=2N=N1.Cl.C(C(N=C=NCCCN(C)C)C)C.C(N(CC)CC)C.[NH2:54][CH2:55][C:56]1[C:57]([OH:64])=[N:58][C:59]([CH3:63])=[CH:60][C:61]=1[CH3:62]>ClCCl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]([NH:54][CH2:55][C:56]3[C:57]([OH:64])=[N:58][C:59]([CH3:63])=[CH:60][C:61]=3[CH3:62])=[O:12])=[C:9]([CH3:14])[N:8]([C@@H:15]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH3:16])[C:6]=2[N:7]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 87594622HCID 87594622, compoundHCID 117778865HCID 117778865, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425225HCID 178425225, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-2-chloro-6-methyl-7-(1-phenylethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid (100 mg, 0.32 mmol) in dichloromethane (10 mL) was added with 1-hydroxybenzotriazole (65 mg, 0.48 mmol), 1-Ethyl-3-(3-dimethylaminopropyl)ethyl-carbodiimide hydrochloride (92 mg, 0.48 mmol) and triethylamine (97 mg, 0.96 mmol). After stirred for 30 minutes, 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (49 mg, 0.32 mmol) was added and the reaction mixture was stirred at room temperature for 12 hours. The solution was concentrated, diluted with water (20 mL), extracted with ethyl acetate (20 mL). The organic layers were separated, combined, dried over anhydrous sodium sulfate, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to afford (R)-2-chloro-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-6-methyl-7-(1-phenylethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide (100 mg, 70%). LRMS (M+H+) m/z: calcd 449.16. found 449.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 12 hours
  2. concentrationThe solution was concentrated
  3. additiondiluted with water (20 mL)
  4. extractionextracted with ethyl acetate (20 mL)
  5. customThe organic layers were separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a residue
  10. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-1130420a5a0743c29ee7dd139c1bd6c4
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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