Triethylamine → HCID 59487300, compound

HRID 1925545Notes

Reaction equation

HRID 1925545 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[F:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][CH2:41][S:42][C:43]2[N:51]=[CH:50][CH:49]=[CH:48][C:44]=2[C:45]([OH:47])=O)=[CH:35][CH:34]=1.[CH3:52][C:53]([CH3:58])([CH3:57])[CH2:54][CH2:55][NH2:56]>C1COCC1.CCCCCC.CC(=O)OCC.CC(=O)OCC>[CH3:52][C:53]([CH3:58])([CH3:57])[CH2:54][CH2:55][NH:56][C:45]([C:44]1[C:43]([S:42][CH2:41][CH2:40][CH2:39][C:36]2[CH:35]=[CH:34][C:33]([F:32])=[CH:38][CH:37]=2)=[N:51][CH:50]=[CH:49][CH:48]=1)=[O:47]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 197093,3-DimethylbutylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67133585HCID 67133585, compound

Product 1

HCID 59487300HCID 59487300, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

274 mg (0.72 mmol) of HATU and 100 ml (0.72 mmol) of NEt3 were added to a solution of 200 mg (0.69 mmol) of 2-(3-(4-fluorophenyl)propylthio)nicotinic acid and 92 ml (0.69 mmol) of 3,3-dimethyl-butylamine in THF (11 ml), and the mixture was stirred for 16 h at RT. Dilution with EA was then carried out. The organic phase was separated off, washed with a 1M aq. Na2CO3 sol. and a 4M aq. NH4Cl sol., dried over MgSO4, filtered and concentrated in vacuo. CC (hexane/EA 2:1) of the residue yielded 173 mg (0.46 mmol, 67%) of N-(3,3-dimethyl-butyl)-2-[3-(4-fluorophenyl)-propylsulfanyl]-pyridine-3-carboxylic acid amide. MS: m/z 375.2 [M+H]+.

Workup

  1. customThe organic phase was separated off
  2. washwashed with a 1M aq. Na2CO3 sol.
  3. dry with materiala 4M aq. NH4Cl sol., dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d34e6703eac343a3b262bdea5a7b1fb3
Source dataset
uspto-grants-2012_05
Patent number
US08178684B2

Reaction notes

Loading…