Ethanolamine → HCID 178509942, compound

HRID 1875226Notes

Reaction equation

HRID 1875226 reaction equation
CS(Cl)(=O)=O.[Br:6][C:7]1[N:8]=[C:9](CO)[NH:10][C:11]=1[C:12]([NH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([O:23][C:24]2[CH:29]=[C:28]([C:30]#[N:31])[CH:27]=[C:26]([Cl:32])[CH:25]=2)[C:17]=1[F:33])=[O:13].[CH3:36][CH2:37][N:38]([CH2:41]C)CC.C(CN)[OH:44]>C(Cl)Cl>[Br:6][C:7]1[N:8]=[C:9]([CH2:41][NH:38][CH2:37][CH2:36][OH:44])[NH:10][C:11]=1[C:12]([NH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([O:23][C:24]2[CH:29]=[C:28]([C:30]#[N:31])[CH:27]=[C:26]([Cl:32])[CH:25]=2)[C:17]=1[F:33])=[O:13]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178509944HCID 178509944, compound

Product 1

HCID 178509942HCID 178509942, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

MsCl (0.020 mL, 0.26 mmol) was added to a solution of 4-bromo-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-2-(hydroxymethyl)-1H-imidazole-5-carboxamide (0.045 g, 0.09 mmol) and Et3N (0.14 mL, 1.00 mmol) in CH2Cl2 (1 mL). After 1 h, ethanolamine (0.20 mL, 3.31 mmol) was added and the reaction mixture was stirred at RT overnight. Purification was achieved by Reverse-Phase HPLC (water:acetonitrile with 0.1% NH4OH). The title compound (0.010, 21%) was isolated as a white solid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.56 (s, 1H), 7.36-7.43 (m, 2H), 7.27 (br. s., 1H), 7.24 (br. s., 1H), 4.64 (s, 2H), 3.86 (s, 2H), 3.66 (t, J=5.36 Hz, 2H), 2.77 (t, J=5.13 Hz, 2H). ES-LCMS: m/z 556.1, 558.4, 560.0 (M+1).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-f4bf22407821421da2f1d6a5609dbf67
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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