Triethylamine → 5-Bromo-2-(3-(3-methoxy-3-oxopropyl)ureido)nicotinic acid

HRID 60440

반응식

HRID 60440 반응식
[CH3:1][O:2][C:3](=[O:9])[CH2:4][CH2:5]C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:17])C=CC=CC=1.C([N:29]([CH2:32]C)CC)C.[NH2:34][C:35]1[N:43]=[CH:42][C:41]([Br:44])=[CH:40][C:36]=1[C:37]([OH:39])=[O:38]>C1(C)C=CC=CC=1.CC(=O)OCC>[Br:44][C:41]1[CH:42]=[N:43][C:35]([NH:34][C:32]([NH:29][CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:9])=[O:17])=[C:36]([CH:40]=1)[C:37]([OH:39])=[O:38]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 77487monoMethyl succinateHCID 199401P,P-Diphenylphosphinic azideHCID 7374452-Amino-5-bromonicotinic acid

생성물 1

HCID 1188754565-Bromo-2-(3-(3-methoxy-3-oxopropyl)ureido)nicotinic acid수율 58.9%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-methoxy-4-oxobutanoic acid (14.6 g, 110.6 mmol) in toluene (530 mL) was added diphenylphosphoryl azide (30.4 g, 110.5 mmol) followed by triethylamine (18.3 g, 181.2 mmol). The reaction was stirred at RT for 30 min then 2-amino-5-bromonicotinic acid (15.9 g, 73.61 mmol) was added. The reaction was refluxed for 6 h, cooled to RT then diluted with EA (530 mL) and washed with brine (2×300 mL). The combined aqueous layers were acidified to PH 5 by adding aq. 2N HCl and a solid formed which was filtered off. The solid was dried to give 5-bromo-2-(3-(3-methoxy-3-oxopropyl)ureido)nicotinic acid (15 g, 39.3% yield) as pale yellow solid. LCMS: MH+ 347 and TR=1.047 min. Used without further purification.

후처리

  1. temperatureThe reaction was refluxed for 6 h
  2. temperaturecooled to RT
  3. washwashed with brine (2×300 mL)
  4. additionby adding aq. 2N HCl
  5. customa solid formed which
  6. filtrationwas filtered off
  7. customThe solid was dried

출처 및 근거

ORD 기록
ord-8209793ed19746dea5047f1b9397dc90
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440972B2

연결된 노트

불러오는 중…