4-Methoxybenzylamine → HCID 117875127, compound

HRID 2283416Notes

Reaction equation

HRID 2283416 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:9][CH3:10])=[C:4]([F:19])[C:3]=1[C:20]([C:22]1[CH:23]=[N:24][C:25](Cl)=[CH:26][CH:27]=1)=[O:21].[CH3:29][O:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH2:36])=[CH:33][CH:32]=1>CS(C)=O.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:9][CH3:10])=[C:4]([F:19])[C:3]=1[C:20]([C:22]1[CH:23]=[N:24][C:25]([NH:36][CH2:35][C:34]2[CH:37]=[CH:38][C:31]([O:30][CH3:29])=[CH:32][CH:33]=2)=[CH:26][CH:27]=1)=[O:21]

Participants

5

Reactant 2

HCID 754524-MethoxybenzylamineHCID 89544738HCID 89544738, compound

Product 1

HCID 117875127HCID 117875127, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Step 7—To a solution of tert-butyl N-[(1R)-1-[4-chloro-3-(6-chloropyridine-3-carbonyl)-2-fluorophenyl]propyl]-carbamate (82.8 g, 194 mmol) from Step 6 in DMSO (5 vol) was added 4-methoxybenzylamine (53.1 g, 2 equi Vol). The mixture was heated to 50° C. (external temp) overnight then allowed to cool. The mixture was diluted with EtOAc (30 vol) and washed with 5% citric acid (5 vol), water (5 vol) and brine (5 vol) and concentrated to furnish tert-butyl N-[(1R)-1-[4-chloro-2-fluoro-3-(6-{[(4-methoxyphenyl)methyl]amino}pyridine-3-carbonyl)phenyl]propyl]carbamate as a brown oil, 109 g. m/z: 528.

Workup

  1. temperatureto cool
  2. washwashed with 5% citric acid (5 vol), water (5 vol) and brine (5 vol)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-15a7ad2edb8944c7a4dda5e1837d67b5
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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