1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Phenylbenzo[d]oxazole-4-carboxamide

HRID 415235ノート

反応式

HRID 415235 の反応式
[C:1]1([C:7]2[O:8][C:9]3[C:10](=[C:12]([C:16]([OH:18])=O)[CH:13]=[CH:14][CH:15]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC2N(O)N=[N:25]C=2C=1.[NH4+].[Cl-].CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN(C=O)C.O>[C:1]1([C:7]2[O:8][C:9]3[C:10](=[C:12]([C:16]([NH2:25])=[O:18])[CH:13]=[CH:14][CH:15]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 108683692-Phenylbenzoxazole-4-carboxylic acid

生成物 1

HCID 117763402-Phenylbenzo[d]oxazole-4-carboxamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
25 °C

実験手順

To a solution of 2-phenylbenzo[d]oxazole-4-carboxylic acid in DMF (15 mL) was added HOBt (148 mg, 1.1 mmol), NH4Cl (54 mg, 1.0 mmol), DIPEA (387 mg, 3.0 mmol) and EDCI (211 mg, 1.1 mmol). The mixture was stirred at 25° C. for 10 hr. Then water (10 mL) was added and aqueous hydrochloric acid (1 N) to pH=3 and extracted with ethyl acetate (100 mL×4). The organic phase was washed with saturated sodium bicarbonate solution and brine, concentrated and dried in vacuum. The crude product was purified by pre-HPLC to obtain 2-phenylbenzo[d]oxazole-4-carboxamide as a white solid (40 mg). 1H-NMR (400 MHz, DMSO-d6) δ 7.47-7.56 (m, 1H), 7.63-7.68 (m, 3H), 7.93-8.01 (m, 3H), 8.28-8.30 (d, J=8 Hz, 2H), 8.47 (s, 1H); LC-MS (ESI) m/z 239 [M+1]+.

後処理

  1. extractionaqueous hydrochloric acid (1 N) to pH=3 and extracted with ethyl acetate (100 mL×4)
  2. washThe organic phase was washed with saturated sodium bicarbonate solution and brine
  3. concentrationconcentrated
  4. customdried in vacuum
  5. customThe crude product was purified by pre-HPLC

出典と根拠

ORDレコード
ord-735ab54c650c4917a9642fd196d03bc4
出典データセット
uspto-grants-2012_01
特許番号
US08088760B2

反応ノート

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