Lithium Hydroxide → 2-(6-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-2-ethyl-4-oxoquinazolin-3(4H)-yl)acetic acid

HRID 77380

반응식

HRID 77380 반응식
[NH2:1][C:2]1[CH:14]=[CH:13][C:12]([N:15]2[CH:21]3[CH2:22][CH2:23][N:18]([CH2:19][CH2:20]3)[CH2:17][CH2:16]2)=[CH:11][C:3]=1[C:4]([NH:6][CH2:7][C:8]([OH:10])=[O:9])=[O:5].[OH-].[Li+].C(O[C:29](OCC)(OCC)[CH2:30][CH3:31])C>CO>[N:18]12[CH2:23][CH2:22][CH:21]([CH2:20][CH2:19]1)[N:15]([C:12]1[CH:11]=[C:3]3[C:2](=[CH:14][CH:13]=1)[N:1]=[C:29]([CH2:30][CH3:31])[N:6]([CH2:7][C:8]([OH:10])=[O:9])[C:4]3=[O:5])[CH2:16][CH2:17]2

참가 물질

5

반응물 3

HCID 3939Lithium HydroxideHCID 66995Ethyl orthopropionateHCID 671147142-(2-Amino-5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)benzamido)acetic acid2회

생성물 1

HCID 699285972-(6-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-2-ethyl-4-oxoquinazolin-3(4H)-yl)acetic acid

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
160 °C

실험 절차

2-(2-Amino-5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)benzamido)acetic acid (85.3 mg, 0.27 mmol) (Intermediate 9A) (100 mg, 0.36 mmol) was dissolved in triethoxypropane (1 mL), and heated in the microwave at 160° C. for 10 minutes. Reaction allowed to cool to room temperature and lithium hydroxide solution added (0.5 mL, 1M in methanol) and reaction stirred overnight. Organic layer purified using a 1 g SCX cartridge, followed by preparative-HPLC. Purified sample was free-based using 500 mg SCX cartridge to afford 2-(6-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-2-ethyl-4-oxoquinazolin-3(4H)-yl)acetic acid (76 mg, 0.21 mmol).

후처리

  1. customReaction
  2. temperatureto cool to room temperature
  3. customOrganic layer purified
  4. customPurified sample

출처 및 근거

ORD 기록
ord-8084490e27de4145b90648157fce16ca
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841289B2

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