Ammonium formate → HCID 117728268, compound

HRID 61158Notes

Reaction equation

HRID 61158 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[N:5][C:6]([NH:12][CH2:13][C@@H:14]1[C@H:19]([CH3:20])[CH2:18][CH2:17][CH2:16][N:15]1[C:21]([C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=1[N:30]1[N:34]=[CH:33][CH:32]=[N:31]1)=[O:22])=[N:7]2.C([O-])=O.[NH4+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:20][C@@H:19]1[CH2:18][CH2:17][CH2:16][N:15]([C:21]([C:23]2[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=2[N:30]2[N:31]=[CH:32][CH:33]=[N:34]2)=[O:22])[C@@H:14]1[CH2:13][NH:12][C:6]1[N:5]=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][CH:2]=2)[N:7]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 117727815HCID 117727815, compound

Product 1

HCID 117728268HCID 117728268, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ((2S,3R)-2-(((5-bromoquinazolin-2-yl)amino)methyl)-3-methylpiperidin-1-yl)(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone (0.057 g, 0.111 mmol), HCOONH4 (0.14 g, 0.222 mmol) and Pd(PPh3)4 (0.026 g, 0.022 mmol) in dioxane and water (4:1, 2 mL) was heated for 2 h at 100° C. The mixture was cooled to rt and filtered through diatomaceous earth. The solvent was removed and the crude residue was purified via silica gel chromatography to obtain the title compound. ESI-MS (m/z): 442 [M+1]+.

Workup

  1. temperatureThe mixture was cooled to rt
  2. filtrationfiltered through diatomaceous earth
  3. customThe solvent was removed
  4. customthe crude residue was purified via silica gel chromatography

Sources & evidence

ORD record
ord-e335bafc470c432e895b59949de942d2
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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