Hydrochloric Acid → [3-(2,2-Difluoro-2-pyridin-2-yl-ethylamino)-2-oxo-2h-pyrazin-1-yl]acetic acid

HRID 1795292노트

반응식

HRID 1795292 반응식
C([O:3][C:4](=[O:24])[CH2:5][N:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH:12][CH2:13][C:14]([F:22])([F:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[C:7]1=[O:23])C.[OH-].[Li+].Cl>CO.CCOCC>[F:22][C:14]([F:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[CH2:13][NH:12][C:8]1[C:7](=[O:23])[N:6]([CH2:5][C:4]([OH:24])=[O:3])[CH:11]=[CH:10][N:9]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 10290909[3-(2,2-difluoro-2-pyridin-2-yl-ethylamino)-2-oxo-2H-pyrazin-1-yl]-acetic acid ethyl ester

생성물 1

HCID 22185125[3-(2,2-Difluoro-2-pyridin-2-yl-ethylamino)-2-oxo-2h-pyrazin-1-yl]acetic acid

시약·촉매·용매 2

HCID 887Methanol용매HCID 3283Diethyl Ether용매

실험 절차

To a solution of 2.84 g (8.41 mmol) [3-(2,2-difluoro-2-pyridin-2-yl-ethylamino)-2oxo-2H-pyrazin-1-yl]-acetic acid ethyl ester (preparation described in example 17, step K) in 10.0 mL methanol was added 8.83 mL (8.83 mmol) 1.0N lithium hydroxide (aq) and the light yellow solution stirred 1 h at room temperature. The reaction pH was adjusted to 7.0 with a dropwise addition of 1.0N HCl in ether to give a precipitate. The solid was removed by filtration, washed well with water and dried under high vacuum for 24 h to give 3-[2,2-Difluoro-2-pyridin-2-yl-ethylamino)-2-oxo-2H-pyrazin-1-yl]acetic acid as a white solid: 1H NMR (DMSO-d6, 400 MHz): δ 13.13 (br s, 1H), 8.70 (d, 1H, J=4.7 Hz), 7.98 (t, 1H, J=7.8 Hz), 7.70 (d, 1H, J=7.9 Hz), 7.60–7.55 (m, 1H), 7.16 (t, 1H, J=6.7 Hz), 6.84 (d, 1H, J=4.7 Hz), 6.73 (d, 1H, J=4.6 Hz), 4.57 (s, 2H), 4.24 (dt, 2H, J=6.6 and 15.2 Hz); MS (Electrospray): M+H=311.0.

후처리

  1. customto give a precipitate
  2. customThe solid was removed by filtration
  3. washwashed well with water
  4. customdried under high vacuum for 24 h
  5. customto give 3-[2,2-Difluoro-2-pyridin-2-yl-ethylamino)-2-oxo-2H-pyrazin-1-yl]acetic acid as a white solid

출처 및 근거

ORD 기록
ord-5ea920d2ff67417cb8110eabba67261b
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07026324B2

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