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

HRID 60440

反応式

HRID 60440 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8209793ed19746dea5047f1b9397dc90
出典データセット
uspto-grants-2016_09
特許番号
US09440972B2

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