Triethylamine → HCID 86703244, compound

HRID 2204423Notes

Reaction equation

HRID 2204423 reaction equation
CS(OS(C)(=O)=O)(=O)=O.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17](O)[C:18]2[N:19]([CH:27]3[CH2:29][CH2:28]3)[CH:20]=[CH:21][C:22]=2[C:23]([O:25][CH3:26])=[O:24])=[CH:13][CH:12]=1.C(N(CC)CC)C.[NH2:38][C:39]1[CH:40]=[C:41]([CH3:47])[C:42](=[O:46])[N:43]([CH3:45])[CH:44]=1>C(Cl)Cl>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([NH:38][C:39]2[CH:40]=[C:41]([CH3:47])[C:42](=[O:46])[N:43]([CH3:45])[CH:44]=2)[C:18]2[N:19]([CH:27]3[CH2:29][CH2:28]3)[CH:20]=[CH:21][C:22]=2[C:23]([O:25][CH3:26])=[O:24])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 674566165-Amino-1,3-dimethyl-1,2-dihydropyridin-2-oneHCID 86703245HCID 86703245, compound

Product 1

HCID 86703244HCID 86703244, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonic anhydride (3.42 g, 19.62 mmol) was added at −40° C. to a stirred solution of methyl 2-((4-chlorophenyl)(hydroxy)methyl)-1-cyclopropyl-1H-pyrrole-3-carboxylate (Step 240.5) (3 g, 9.81 mmol) and triethylamine (6.84 mL, 49.1 mmol) in CH2Cl2 (60 mL). After 15 min at −40° C., 5-amino-1,3-dimethylpyridin-2(1H)-one (Step 240.7) (1.762 g, 12.76 mmol) was added. The resulting mixture was allowed to warm from −40° C. to rt over 18 hr under stirring, diluted in CH2Cl2//water, and extracted twice with CH2Cl2. The combined organic extracts were dried and concentrated. The crude material was purified by silica gel column chromatography (CH2Cl2/MeOH 97.5:2.5) to afford the title compound (2.2 g, 51.6% yield) as a brown foam. tR: 1.13 min (LC-MS 6); ESI-MS: 426.2 [M+H]+ (LC-MS 6); TLC (CH2Cl2/MeOH 97.5:2.5): Rf=0.29.

Workup

  1. temperatureto warm from −40° C. to rt over 18 hr
  2. extractionextracted twice with CH2Cl2
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated
  5. customThe crude material was purified by silica gel column chromatography (CH2Cl2/MeOH 97.5:2.5)

Sources & evidence

ORD record
ord-df1cec902ee14840be164c684b4cf5a2
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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