Carbamic acid, 4-pyridinyl-, phenyl ester → HCID 86670994, compound

HRID 515368Notes

Reaction equation

HRID 515368 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([CH:10]3[CH2:15][CH2:14][N:13]([CH2:16][C:17]4[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=4)[CH2:12][CH2:11]3)[C:6]=2[CH:33]=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:29][C:28]([F:31])([F:30])[C:23]([C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:13]2[CH2:12][CH2:11][CH:10]([N:7]3[C:6]4[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]=[CH:4][C:5]=4[N:9]=[CH:8]3)[CH2:15][CH2:14]2)=[CH:18][CH:19]=1)([OH:32])[C:24]([F:25])([F:26])[F:27]

Participants

4

Reactant 2

HCID 11401617Carbamic acid, 4-pyridinyl-, phenyl esterHCID 86670993HCID 86670993, compound

Product 1

HCID 86670994HCID 86670994, compoundYield 12.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-(4-((4-(6-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 (16 mg).

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-2a990646fdac452ca275d010bfa5f24e
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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