Triethylamine → HCID 22137343, compound

HRID 1827547Notes

Reaction equation

HRID 1827547 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][O:25]4)[CH:18]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:37][C:38]1[CH:46]=[C:45]([Cl:47])[CH:44]=[C:43]([Cl:48])[C:39]=1[C:40](Cl)=[O:41]>C(Cl)Cl>[Cl:37][C:38]1[CH:46]=[C:45]([Cl:47])[CH:44]=[C:43]([Cl:48])[C:39]=1[C:40]([N:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][N:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)=[CH:10][CH:11]=1)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH:18]=1)=[O:41]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 22137433[4-(2-Pyrrolidin-1-yl-ethoxy)-phenyl]-[3-(tetrahydro-pyran-2-yloxy)-benzyl]-amine

Product 1

HCID 22137343HCID 22137343, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-[3-(tetrahydro-pyran-2-yloxy)-benzyl]-amine (0.050 g, 0.13 mmol) in 0.5 mL methylene chloride was added triethylamine (0.035 mL, 0.25 mmol), 2,4,6-trichlorobenzoyl chloride (0.061 g, 0.25 mmol), and catalytic N,N-dimethylaminopyridine (DMAP). The reaction mixture was stirred overnight at room temperature. The reaction was concentrated to give the title compound of Step A which was used in Step B without further purification. MS 605.4 (M+1)+

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-4aece03e0bae4bb3847e2d9646f2a078
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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