N-methyl-2-pyrrolidone → HCID 11711258, compound

HRID 1639972Notes

Reaction equation

HRID 1639972 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][C:10]2([CH2:17][CH2:16][CH2:15][NH:14][CH2:13]2)[C:9]1=[O:18].Cl[C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][N:21]=1.C(N(CC)C(C)C)(C)C.CN1CCCC1=O>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][C:10]2([CH2:17][CH2:16][CH2:15][N:14]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][N:21]=3)[CH2:13]2)[C:9]1=[O:18]

Participants

5

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 66722206HCID 66722206, compound

Product 1

HCID 11711258HCID 11711258, compound

Conditions

Temperature
180 °C

Procedure

A mixture of 2-(2-chlorophenyl)-2,7-diazaspiro[4.5]decan-1-one (16.0 mg, 0.0000604 mol, which was prepared by using a procedure that was analogous to that used for the synthesis of example 92, steps 1-4), 2-chloro-5-(trifluoromethyl)pyridine (13 mg, 0.000072 mol) and N,N-diisopropylethylamine (0.032 mL, 0.00018 mol) in N-methylpyrrolidinone (0.4 mL, 0.005 mol) was irradiated with microwaves to heat the reaction mixture to 180° C. for 20 min. The crude product was purified by prep-HPLC to afford the desired product. LC-MS: 410.2/412.2 (M+H)+.

Workup

  1. customwas prepared
  2. customwas irradiated with microwaves
  3. customThe crude product was purified by prep-HPLC

Sources & evidence

ORD record
ord-bc9f1904ded14701a40a48d623e7cded
Source dataset
uspto-grants-2012_02
Patent number
US08110581B2

Reaction notes

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