Diisopropylethylamine → HCID 58065458, compound

HRID 1964604Notes

Reaction equation

HRID 1964604 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]([OH:18])=O)=[N:14][CH:15]=1.Cl.[NH:34]1[CH2:37][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>[N:34]1([C:16]([C:13]2[CH:12]=[N:11][C:10]([O:9][C:8]3[CH:19]=[C:20]([C:22]4[NH:23][C:24]([C:27]5[S:28][CH:29]=[CH:30][N:31]=5)=[CH:25][CH:26]=4)[CH:21]=[C:6]([O:5][C@@H:4]([CH3:32])[CH2:3][O:2][CH3:1])[CH:7]=3)=[CH:15][N:14]=2)=[O:18])[CH2:37][CH2:36][CH2:35]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12308726Azetidine hydrochlorideHCID 66682402HCID 66682402, compound

Product 1

HCID 58065458HCID 58065458, compoundYield 96%

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]phenoxy}pyrazine-2-carboxylic acid (28.0 mg, 0.062 mmol) synthesized in Example (63a) was dissolved in tetrahydrofuran (3 mL), and azetidine hydrochloride (17.4 mg, 0.186 mmol), HATU (35.3 mg, 0.093 mmol) and N,N-diisopropylethylamine (65 μL, 0.37 mmol) were added, followed by stirring at room temperature for 28 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 preparative TLC (developing solvent: methanol/dichloromethane=15%) to afford the desired compound (29.1 mg, yield 96%) as a white 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

Sources & evidence

ORD record
ord-7069b569e8ce401e915b9994061e64a9
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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