1-Methylpiperazine → HCID 58065509, compound

HRID 909538Notes

Reaction equation

HRID 909538 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]([CH3:32])[O:5][C:6]1[CH:7]=[C:8]([CH:19]=[C:20]([C:22]2[NH:23][C:24]([C:27]3[S:28][CH:29]=[CH:30][N:31]=3)=[CH:25][CH:26]=2)[CH:21]=1)[O:9][C:10]1[N:11]=[CH:12][C:13]([C:16](O)=[O:17])=[N:14][CH:15]=1.[CH3:33][N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>O1CCCC1.O>[CH3:1][O:2][CH2:3][C@H:4]([CH3:32])[O:5][C:6]1[CH:7]=[C:8]([CH:19]=[C:20]([C:22]2[NH:23][C:24]([C:27]3[S:28][CH:29]=[CH:30][N:31]=3)=[CH:25][CH:26]=2)[CH:21]=1)[O:9][C:10]1[CH:15]=[N:14][C:13]([C:16]([N:37]2[CH2:38][CH2:39][N:34]([CH3:33])[CH2:35][CH2:36]2)=[O:17])=[CH:12][N:11]=1

Participants

7

Reactant 4

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66682402HCID 66682402, compound

Product 1

HCID 58065509HCID 58065509, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxyl}pyrazine-2-carboxylic acid (40.4 mg, 0.089 mmol) synthesized in Example (63a) was dissolved in tetrahydrofuran (5 mL), and 1-methylpiperazine (30 μL, 0.27 mmol), HATU (67.9 mg, 0.18 mmol) and N,N-diisopropylethylamine (93 μL, 0.54 mmol) were added, followed by stirring at room temperature for 12 hours under nitrogen atmosphere. To the reaction solution, water (15 mL) was added, and extraction was carried out with ethyl acetate (15 mL), followed by drying over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: methanol/dichloromethane=0%-5%) to afford the desired compound (47 mg, yield 98%) as a pale yellow solid.

Workup

  1. extractionextraction
  2. dry with materialby drying over sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe resulting residue was purified
  5. washsilica gel column chromatography (elution solvent: methanol/dichloromethane=0%-5%)

Sources & evidence

ORD record
ord-11c1f56eb2724380b67c86d8089eeef9
Source dataset
uspto-grants-2011_09
Patent number
US08017610B2

Reaction notes

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