Ethyl Acetate → 1-[2-(3-Hydroxyphenyl)thiazol-4-yl]-3-(6-piperidin-1-ylmethyl-pyridin-2-yl)urea

HRID 460258노트

반응식

HRID 460258 반응식
CO[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[S:10][CH:11]=[C:12]([NH:14][C:15]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[N:19]=2)=[O:16])[N:13]=1.[Cl-].[Be+2].[Cl-].CC[O:36]C(C)=O>C1(C)C=CC=CC=1>[OH:36][C:6]1[CH:5]=[C:4]([C:9]2[S:10][CH:11]=[C:12]([NH:14][C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][N:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)[N:19]=3)=[O:16])[N:13]=2)[CH:3]=[CH:8][CH:7]=1

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 24588Beryllium ChlorideHCID 187721331-[2-(2-Methoxyphenyl)thiazol-4-yl]-3-(6-piperidin-1-ylmethyl-pyridin-2-yl)urea

생성물 1

HCID 187716961-[2-(3-Hydroxyphenyl)thiazol-4-yl]-3-(6-piperidin-1-ylmethyl-pyridin-2-yl)urea

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

A mixture of 1-[2-(3-methoxyphenyl)thiazol-4-yl]-3-(6-piperidin-1-ylmethyl-pyridin-2-yl)urea (Example 218) and beryllium chloride (5.0 eq) in dry toluene (0.2 M) and 4A molecular sieves was heated at reflux for 10 h. The starting material was not totally soluble in toluene. The mixture was brought to RT, diluted with EtOAc and washed with saturated NH4Cl. The organic phase was separated, dried over MgSO4, filtered, concentrated by rotary evaporation and purified by prep HPLC (Column Phenomenex type Prodigy 50 ODS3 100A size 250×21.20 mm 5 u, Gradient 10% to 90% CH3CN:H2O containing 1% TFA over 20 min, Detector 254 nm, 4 nm Band) to afford the title compound as an off white solid. EI-MS m/z 410 (M+H). Calc'd for C21H23N5O2S: 409.16.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 10 h
  3. customwas brought to RT
  4. washwashed with saturated NH4Cl
  5. customThe organic phase was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation
  9. custompurified by prep HPLC (Column Phenomenex type Prodigy 50 ODS3 100A size 250×21.20 mm 5 u, Gradient 10% to 90% CH3CN:H2O containing 1% TFA over 20 min, Detector 254 nm, 4 nm Band)

출처 및 근거

ORD 기록
ord-cee1b718063648dcb6195417a281cd91
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196104B2

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