Triethylamine → HCID 58379622, compound

HRID 1630354Notes

Reaction equation

HRID 1630354 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:28]4[CH:29]=[N:30][C:31]5[C:36]([CH:37]=4)=[CH:35][CH:34]=[CH:33][CH:32]=5)[N:26]=3)[N:21]=[CH:20][C:19]=2C(O)=O)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.[CH2:41]([N:43]([CH2:46]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:55])C=CC=CC=1>CN(C)C=O>[CH3:41][N:43]1[C:19]2[CH:20]=[N:21][C:22]3[CH:23]=[CH:24][C:25]([C:28]4[CH:29]=[N:30][C:31]5[C:36]([CH:37]=4)=[CH:35][CH:34]=[CH:33][CH:32]=5)=[N:26][C:27]=3[C:18]=2[N:17]([CH:14]2[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]2)[C:46]1=[O:55]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 58379645HCID 58379645, compound

Product 1

HCID 58379622HCID 58379622, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of compound 47 (7.8 g, 15 mmol) and triethylamine (4.1 mL, 29 mmol) in N,N-dimethylformamide (200 mL) was stirred at room temperature for 2 hr. Diphenyl phosphoryl azide (6.5 mL, 29 mmol) was added dropwise to the suspension via a syringe pump. After stirring 2 hours at room temperature the mixture was heated to 60° C., resulting in a solution. After 1.5 hr the reaction was cooled to room temperature overnight. The precipitate was collected by filtration to afford the title compound (4.2 g, 54%). The filtrate was concentrated and the residue was triturated with methanol to afford benzyl 4-(2-oxo-8-quinolin-3-yl-2,3-dihydro-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)piperidine-1-carboxylate (compound 48) (2.7 g, 35%).

Workup

  1. stirringAfter stirring 2 hours at room temperature the mixture
  2. temperaturewas heated to 60° C.
  3. customresulting in a solution
  4. temperatureAfter 1.5 hr the reaction was cooled to room temperature overnight
  5. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-0a1fd429a29146e686bd1d713095eb7a
Source dataset
uspto-grants-2014_07
Patent number
US08791131B2

Reaction notes

Loading…