Carbamic acid, 4-pyridinyl-, phenyl ester → HCID 86670996, compound

HRID 515371Notes

Reaction equation

HRID 515371 reaction equation
[NH2:1][C:2]1[CH:33]=[CH:32][C:5]2[N:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][C:16]4[CH:21]=[CH:20][C:19]([C:22]([OH:31])([C:27]([F:30])([F:29])[F:28])[C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=4)[CH2:11][CH2:10]3)[CH:7]=[N:8][C:4]=2[CH:3]=1.[N:34]1[CH:39]=[CH:38][C:37]([NH:40][C:41](=O)[O:42]C2C=CC=CC=2)=[CH:36][CH:35]=1>O1CCOCC1>[F:28][C:27]([F:30])([F:29])[C:22]([C:19]1[CH:18]=[CH:17][C:16]([CH2:15][N:12]2[CH2:13][CH2:14][CH:9]([N:6]3[C:5]4[CH:32]=[CH:33][C:2]([NH:1][C:41]([NH:40][C:37]5[CH:38]=[CH:39][N:34]=[CH:35][CH:36]=5)=[O:42])=[CH:3][C:4]=4[N:8]=[CH:7]3)[CH2:10][CH2:11]2)=[CH:21][CH:20]=1)([OH:31])[C:23]([F:24])([F:25])[F:26]

Participants

4

Reactant 2

HCID 11401617Carbamic acid, 4-pyridinyl-, phenyl esterHCID 86670995HCID 86670995, compound

Product 1

HCID 86670996HCID 86670996, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-(4-((4-(5-Amino-1H-benzo[d]imidazol-1-yl)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.212 mmol, 0.1 g) and phenyl pyridin-4-ylcarbamate (0.318 mmol, 0.068 g) were combined and heated in a Reactivial in dioxane (2 mL) for 2 days. The solvent was removed and the resulting residue purified by silica chromatography (eluting with a solvent gradient from dichloromethane to 8% methanol/dichloromethane) to afford the title compound (14 mg). MS (ESI) m/z 593.2 [M+H]+

Workup

  1. customThe solvent was removed
  2. customthe resulting residue purified by silica chromatography (
  3. washeluting with a solvent gradient from dichloromethane to 8% methanol/dichloromethane)

Sources & evidence

ORD record
ord-317c06ba919f43e0b2106942029709c6
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

Loading…