1,2-Dichloroethane → 4-Bromo-N-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)-1H-pyrrole-2-carboxamide

HRID 1987920노트

반응식

HRID 1987920 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:7]([OH:9])=O)[NH:5][CH:6]=1.[NH2:10][C:11]1[CH:22]=[CH:21][C:14]([O:15][CH2:16][C:17]([CH3:20])([OH:19])[CH3:18])=[C:13]([O:23][CH3:24])[CH:12]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>ClC(Cl)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:7]([NH:10][C:11]2[CH:22]=[CH:21][C:14]([O:15][CH2:16][C:17]([OH:19])([CH3:20])[CH3:18])=[C:13]([O:23][CH3:24])[CH:12]=2)=[O:9])[NH:5][CH:6]=1

참가 물질

7

반응물 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 27413814-bromo-1H-pyrrole-2-carboxylic acidHCID 595950521-(4-Amino-2-methoxyphenoxy)-2-methylpropan-2-ol

생성물 1

HCID 672152534-Bromo-N-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)-1H-pyrrole-2-carboxamide수율 90.6%

시약·촉매·용매 2

HCID 63651,1-Dichloroethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-bromo-1H-pyrrole-2-carboxylic acid (1.00 g, 5.30 mmol), preparation described in step A of Example 2, and 1-(4-amino-2-methoxyphenoxy)-2-methylpropan-2-ol (1.12 g, 5.30 mmol), preparation described in step A of Example 4. in dichloroethane (46.0 mL) was added EDC (2.03 g, 10.6 mmol) and HOBT (1.62 g, 10.6 mmol) and the reaction was allowed to stir at rt for 16 h. The reaction mixture was diluted with EtOAc (100 mL), washed with sat. NaHCO3 (3×100 mL), water, brine, dried over anhydrous Na2SO4 and concentrated to give 1.84 g of the title compound as a brown oil which was used in the next step without purification: HPLC a) column: Phenomenex Luna 5μ 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% H3PO4 to 90% MeOH/10% H2O/0.1% H3PO4; 1 min hold, 4 mL/min UV detection at 220 nm, 3.058 min retention time, (91%); HPLC b) column: Phenomenex Luna C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold; 4 mL/min, UV detection at 220 nm, 3.051 min retention time; MS (ES) 385 [M+H]+.

후처리

  1. washwashed with sat. NaHCO3 (3×100 mL), water, brine
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-71b4a0b2807c4f8a841fa85edd0a6e4b
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07553836B2

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