Hydrogen chloride-ethyl acetate → HCID 178483819, compound

HRID 526567Notes

Reaction equation

HRID 526567 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][N:12]([C:15]3[CH:35]=[CH:34][C:18]([C:19]([NH:21][CH2:22][CH2:23][CH2:24][N:25](C)[C:26](=O)OC(C)(C)C)=[O:20])=[CH:17][N:16]=3)[C:13]=2[OH:14])=[CH:5][CH:4]=1)#[N:2].[ClH:36].CCOC(C)=O>CCOC(C)=O>[ClH:36].[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[N:11][N:12]([C:15]3[CH:35]=[CH:34][C:18]([C:19]([NH:21][CH2:22][CH2:23][CH2:24][NH:25][CH3:26])=[O:20])=[CH:17][N:16]=3)[C:13]=2[OH:14])=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 178483820HCID 178483820, compound

Product 1

HCID 178483819HCID 178483819, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combined tert-butyl (3-(6-(4-(4-cyanophenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinamido)propyl)(methyl)carbamate and EtOAc (5 mL) and added HCl-EtOAc (5 mL) and stir at room temperature for 5 h. The reaction mixture was evaporated in vacuo to give the title compound as a yellow green solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.09-9.04 (m, 1H), 9.00 (s, 1H), 8.89 (br. s., 2H), 8.67 (s, 1H), 8.48 (br. s., 2H), 8.15 (d, J=8.2 Hz, 2H), 7.79 (d, J=8.4 Hz, 2H), 3.38 (d, J=6.0 Hz, 2H), 2.95 (br. s., 2H), 2.54 (t, J=5.3 Hz, 3H), 1.96-1.85 (m, 2H). MS m/Z [M+H]+ 377.1.

Workup

  1. customThe reaction mixture was evaporated in vacuo

Sources & evidence

ORD record
ord-0e5a82307c75402ba38215af3b375284
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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