tert-Butyl piperazine-1-carboxylate → 4-{(S)-1-[3-(1-Methyl-1H-benzoimidazol-2-yl)-phenyl]-piperidine-3-carbonyl}-piperazine-1-carboxylic acid tert-butyl ester

HRID 77087Notes

Reaction equation

HRID 77087 reaction equation
[CH3:1][N: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:17]2[CH2:22][CH2:21][CH2:20][C@H:19]([C:23](O)=[O:24])[CH2:18]2)[CH:14]=[CH:15][CH:16]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:50]([O:54][C:55]([N:57]1[CH2:62][CH2:61][NH:60][CH2:59][CH2:58]1)=[O:56])([CH3:53])([CH3:52])[CH3:51]>>[C:50]([O:54][C:55]([N:57]1[CH2:62][CH2:61][N:60]([C:23]([C@H:19]2[CH2:20][CH2:21][CH2:22][N:17]([C:13]3[CH:14]=[CH:15][CH:16]=[C:11]([C:3]4[N:2]([CH3:1])[C:6]5[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=5[N:4]=4)[CH:12]=3)[CH2:18]2)=[O:24])[CH2:59][CH2:58]1)=[O:56])([CH3:53])([CH3:51])[CH3:52]

Participants

4

Reactant 3

HCID 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 66977661HCID 66977661, compound

Product 1

HCID 669774704-{(S)-1-[3-(1-Methyl-1H-benzoimidazol-2-yl)-phenyl]-piperidine-3-carbonyl}-piperazine-1-carboxylic acid tert-butyl esterYield 27%

Conditions

Temperature
35 °C

Procedure

Method A—Step a To a vial with (S)-1-[3-(1-Methyl-1H-benzoimidazol-2-yl)-phenyl]-piperidine-3-carboxylic acid (0.10 g, 0.30 mmol) (obtained as described in general method 1, step d), HATU (0.12 g, 0.31 mmol), TEA (0.09 mL, 0.66 mmol) and tert-Butyl-1-piperazinecarboxylate (0.07 g, 0.37 mmol) dichloromethane (2 mL) 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 0.04 g of the title compound (27%).

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-b4685e74b90049c4992d4ce746b4a37f
Source dataset
uspto-grants-2014_09
Patent number
US08835648B2

Reaction notes

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