1-Chloro-N,N-2-trimethylpropenylamine → HCID 86703121, compound

HRID 2204316Notes

Reaction equation

HRID 2204316 reaction equation
ClC(N(C)C)=C(C)C.[Cl:9][C:10]1[C:15](=[O:16])[N:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[CH:13]=[C:12]([NH:26][CH:27]([C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=2)[C:28]2[N:29]([CH:36]([CH3:38])[CH3:37])[CH:30]=[CH:31][C:32]=2[C:33]([OH:35])=O)[CH:11]=1>C(Cl)Cl>[Cl:9][C:10]1[C:15](=[O:16])[N:14]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)[CH:13]=[C:12]([N:26]2[C:33](=[O:35])[C:32]3[CH:31]=[CH:30][N:29]([CH:36]([CH3:37])[CH3:38])[C:28]=3[CH:27]2[C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=2)[CH:11]=1

Participants

4

Reactant 2

HCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 86703122HCID 86703122, compound

Product 1

HCID 86703121HCID 86703121, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-Chloro-N,N,2-trimethylpropenylamine [26189-59-3] (2.90 mmol) was added to a solution of 2-[[5-chloro-1-(4-methoxy-benzyl)-6-oxo-1,6-dihydro-pyridin-3-ylamino]-(4-chloro-phenyl)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid (Step O2) (1.943 mmol) in CH2Cl2 (20 mL) at 0° C. After stirring for 2 h, the reaction mixture was diluted with CH2Cl2 and successively washed with a saturated aqueous solution of NaHCO3 and brine, dried (Na2SO4), filtered and concentrated. The residue was purified using a RediSep® silica gel column to afford the title compound as a light brown solid. tR: 6.81 min (HPLC 2); ESI-MS: tR=1.13 min, [M+H]+ 522/524/526 (LC-MS 1); TLC: Rf=0.48 (EtOAc).

Workup

  1. washsuccessively washed with a saturated aqueous solution of NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified

Sources & evidence

ORD record
ord-67a3874aec274e3a8af4ffc57cb6eaa6
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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