Carbamic acid, 4-pyridinyl-, phenyl ester → HCID 86670998, compound

HRID 515376Notes

Reaction equation

HRID 515376 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH:11]3[CH2:16][CH2:15][N:14]([CH2:17][C:18]4[CH:23]=[CH:22][C:21]([C:24]([OH:33])([C:29]([F:32])([F:31])[F:30])[C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=4)[CH2:13][CH2:12]3)[N:7]=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:30][C:29]([F:32])([F:31])[C:24]([C:21]1[CH:20]=[CH:19][C:18]([CH2:17][N:14]2[CH2:13][CH2:12][CH:11]([N:6]3[CH:5]=[C:4]4[C:8]([CH:9]=[CH:10][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]4)=[N:7]3)[CH2:16][CH2:15]2)=[CH:23][CH:22]=1)([OH:33])[C:25]([F:26])([F:27])[F:28]

Participants

4

Reactant 2

HCID 11401617Carbamic acid, 4-pyridinyl-, phenyl esterHCID 86670999HCID 86670999, compound

Product 1

HCID 86670998HCID 86670998, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-(4-((4-(5-Amino-2H-indazol-2-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 stirred in dioxane (2 mL) at 100° C. in a Reactivial. The solvent was removed and the resulting residue was purified by silica chromatography (eluting with a solvent gradient from dichloromethane to 8% methanol/dichloromethane) to afford the title compound (14 mg).

Workup

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

Sources & evidence

ORD record
ord-36a03d851d3a47a994e9f16791dcfdd0
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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