Triethylamine → HCID 66977793, compound

HRID 77089Notes

Reaction equation

HRID 77089 reaction equation
Cl.[NH:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[C:11]1[CH:12]=[C:13]([N:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([C:24](O)=[O:25])[CH2:19]2)[CH:14]=[CH:15][C:16]=1[Cl:17].CN(C(ON1N=NC2[CH:38]=[CH:39][CH:40]=[N:41][C:36]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.C(OC(N1CCNCC1)=O)(C)(C)C>>[NH:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:2]=[C:3]1[C:11]1[CH:12]=[C:13]([N:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([C:24]([N:41]3[CH2:40][CH2:39][CH2:38][CH2:36]3)=[O:25])[CH2:19]2)[CH:14]=[CH:15][C:16]=1[Cl:17]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66977814(R)-1-[3-(1H-Benzoimidazol-2-yl)-4-chloro-phenyl]-piperidine-3-carboxylic acid hydrochloride

Product 1

HCID 66977793HCID 66977793, compoundYield 55%

Conditions

Temperature
35 °C

Procedure

Method B—Step a To a vial with (R)-1-[3-(1H-Benzoimidazol-2-yl)-4-chloro-phenyl]-piperidine-3-carboxylic acid hydrochloride (obtained as described in general method 2, step e) (0.10 g, 0.28 mmol) (obtained as described in general method 2), HATU (0.11 g, 0.30 mmol), triethylamine (TEA) (0.09 mL, 0.66 mmol) and tert-Butyl-1-piperazinecarboxylate (0.08 g, 0.62 mmol) dichloromethane (2 L) was added and the reaction mixture was heated at 35° C. overnight. Reaction was cooled to room temperature, solvent removed and the crude purified by preparative HPLC and NH2 column filtration, to obtain 0.06 g of the title compound (55%).

Workup

  1. customReaction
  2. temperaturewas cooled to room temperature
  3. customsolvent removed
  4. filtrationthe crude purified by preparative HPLC and NH2 column filtration

Sources & evidence

ORD record
ord-3240fcc059bb439db51165dca8c83c8e
Source dataset
uspto-grants-2014_09
Patent number
US08835648B2

Reaction notes

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