tert-Butanol → HCID 90731614、化合物

HRID 1800434ノート

反応式

HRID 1800434 の反応式
[CH:1]1([C:4]([NH:6][C:7]2[S:8][C:9]3[C:14]([N:15]=2)=[CH:13][CH:12]=[C:11]([O:16][C:17]2[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=2[O:26][CH3:27])C(O)=O)[N:10]=3)=[O:5])[CH2:3][CH2:2]1.[CH3:28][C:29]([OH:32])([CH3:31])[CH3:30].C([N:35]([CH2:38]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:47])C=CC=CC=1>CN(C)C=O.O>[C:29]([O:32][C:38](=[O:47])[NH:35][C:19]1[CH:23]=[CH:24][C:25]([O:26][CH3:27])=[C:17]([O:16][C:11]2[N:10]=[C:9]3[S:8][C:7]([NH:6][C:4]([CH:1]4[CH2:2][CH2:3]4)=[O:5])=[N:15][C:14]3=[CH:13][CH:12]=2)[CH:18]=1)([CH3:31])([CH3:30])[CH3:28]

参加物

7

反応物 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 86645992HCID 86645992、化合物

生成物 1

HCID 90731614HCID 90731614、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

To a solution of 3-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-methoxybenzoic acid (1.92 g, 4.98 mmol) produced in Example C4(v) in N,N-dimethylformamide (50 mL) and 2-methylpropan-2-ol (50 mL) were added triethylamine (5 mL, 35.9 mmol) and diphenylphosphoryl azide (3 mL, 13.9 mmol), and the mixture was stirred at 120° C. for 2 hr. After cooling the reaction solution to room temperature, the reaction solution was diluted with water (200 mL). The yielded solid was collected by filtration to give tert-butyl[3-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-methoxyphenyl]carbamate (primary product, 1.16 g). The filtrate was extracted with ethyl acetate-hexane (1:1, 150 mL×3), and the combined organic layer was washed with saturated brine (150 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, the filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (ethyl acetate/hexane=2/98→80/20) to give tert-butyl[3-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-methoxyphenyl]carbamate (secondary product, 994 mg). These products contained structurally unknown impurities but used for the next reaction without further purification.

後処理

  1. temperatureAfter cooling the reaction solution to room temperature
  2. filtrationThe yielded solid was collected by filtration

出典と根拠

ORDレコード
ord-42c037047a9d41efaf7731ec544cc6e4
出典データセット
uspto-grants-2013_01
特許番号
US08344135B2

反応ノート

読み込み中…