Triethylamine → HCID 178454574, compound

HRID 707308Notes

Reaction equation

HRID 707308 reaction equation
Cl.[Cl:2][C:3]1[C:8]([C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=O)=[CH:7][CH:6]=[CH:5][N:4]=1.[S:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[NH:24][C@H:25]1[CH2:28][C@H:27]([NH2:29])[CH2:26]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>ClCCl.O>[S:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[NH:24][C@H:25]1[CH2:26][C@H:27]([NH:29][C:10](=[O:12])[C:9]([C:8]2[C:3]([Cl:2])=[N:4][CH:5]=[CH:6][CH:7]=2)([CH3:14])[CH3:13])[CH2:28]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86694174HCID 86694174, compoundHCID 178511738HCID 178511738, compound

Product 1

HCID 178454574HCID 178454574, compoundYield 60.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Intermediate 25 (216 mg, 1.083 mmol), intermediate 11 (198 mg, 0.903 mmol), HBTU (376 mg, 0.993 mmol) and triethylamine (377 μl, 2.71 mmol) were dissolved in dichloromethane (20 mL). The reaction mixture was stirred at room temperature for 14 hours. The reaction mixture was diluted with water and extracted with dichloromethane. The organic extract was washed with saturated ammonium chloride and dried over magnesium sulfate. The solution was concentrated in vacuo to give the crude material as a tan solid. The crude material was absorbed onto a plug of silica gel and purified by silica chromatography (hexane to ethyl acetate gradient) to provide N-(trans-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)-2-(2-chloropyridin-3-yl)-2-methylpropanamide (220 mg, 0.549 mmol, 60.8% yield) as white solid.

Workup

  1. extractionextracted with dichloromethane
  2. extractionThe organic extract
  3. washwas washed with saturated ammonium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solution was concentrated in vacuo
  6. customto give the crude material as a tan solid
  7. customThe crude material was absorbed onto a plug of silica gel
  8. custompurified by silica chromatography (hexane to ethyl acetate gradient)

Sources & evidence

ORD record
ord-3de7df3d5b17477eaea08e8ebead1492
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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