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

HRID 415235노트

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HRID 415235 반응식
[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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
25 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-735ab54c650c4917a9642fd196d03bc4
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088760B2

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