(5-Bromo-2-chlorophenyl)methanamine → N-[[2-chloro-5-[3-(3,4-dihydro-2H-1-benzopyran-6-yl)-1H-pyrazol-1-yl]phenyl]methyl]acetamide

HRID 1408416Notes

Reaction equation

HRID 1408416 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:13])=[C:6]([CH2:8][NH:9][C:10](=[O:12])[CH3:11])[CH:7]=1.[O:14]1[C:19]2[CH:20]=[CH:21][C:22]([C:24]3[CH:28]=[CH:27][NH:26][N:25]=3)=[CH:23][C:18]=2[CH2:17][CH2:16][CH2:15]1.BrC1C=CC(Cl)=C(CN)C=1>>[Cl:13][C:5]1[CH:4]=[CH:3][C:2]([N:26]2[CH:27]=[CH:28][C:24]([C:22]3[CH:21]=[CH:20][C:19]4[O:14][CH2:15][CH2:16][CH2:17][C:18]=4[CH:23]=3)=[N:25]2)=[CH:7][C:6]=1[CH2:8][NH:9][C:10](=[O:12])[CH3:11]

Participants

4

Reactant 3

HCID 43378979(5-Bromo-2-chlorophenyl)methanamineHCID 67151142N-[(5-bromo-2-chlorophenyl)methyl]acetamide2×HCID 178419929HCID 178419929, compound

Product 1

HCID 67151149N-[[2-chloro-5-[3-(3,4-dihydro-2H-1-benzopyran-6-yl)-1H-pyrazol-1-yl]phenyl]methyl]acetamide

Procedure

N-[(5-bromo-2-chlorophenyl)methyl]acetamide (i.e. the product of Step B) (0.58 g, 2.2 mmol) was reacted with 3-(3,4-dihydro-2H-1-benzopyran-6-yl)-1H-pyrazole (i.e. the product of Step A of Synthesis Example 1) (0.40 g, 2.0 mmol) using a procedure analogous to Step B of Synthesis Example 1 to provide the title product, a compound of the present invention, as a solid (0.09 g).

Workup

  1. customanalogous to Step B of Synthesis Example 1

Sources & evidence

ORD record
ord-012e9908b7a74cf1a0a2a49593ec1225
Source dataset
uspto-grants-2014_12
Patent number
US08921360B2

Reaction notes

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