Water → HCID 89620489, 화합물

HRID 1499994노트

반응식

HRID 1499994 반응식
[Cl:1][C:2]1[C:10]([C:11]2[CH2:15][CH:14]([CH2:16][C:17]#[N:18])[O:13][N:12]=2)=[C:9]([S:19]([CH2:22][CH3:23])(=[O:21])=[O:20])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C([NH:27][C:28]1[N:32]([CH3:33])[N:31]=[N:30][N:29]=1)C=C.C(Cl)(=O)C(Cl)=O.O>N1C=CC=CC=1.ClC(Cl)C>[Cl:1][C:2]1[C:10]([C:11]2[CH2:15][CH:14]([CH2:16][C:17]#[N:18])[O:13][N:12]=2)=[C:9]([S:19]([CH2:22][CH3:23])(=[O:20])=[O:21])[CH:8]=[CH:7][C:3]=1[C:4]([NH:27][C:28]1[N:32]([CH3:33])[N:31]=[N:30][N:29]=1)=[O:5]

참가 물질

7

반응물 4

HCID 962WaterHCID 65578Oxalyl chlorideHCID 54595140HCID 54595140, 화합물HCID 67041496HCID 67041496, 화합물

생성물 1

HCID 89620489HCID 89620489, 화합물

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 63651,1-Dichloroethane용매

반응 조건

온도
75 °C

실험 절차

178 mg (0.5 mmol) of 2-chloro-3-[5-(cyanomethyl)-4,5-dihydro-1,2-oxazol-3-yl]-4-(ethylsulfonyl)benzoic acid and 90 mg (0.65 mmol) of N-allyl-1-methyl-1H-tetrazol-5-amine are stirred in 3 ml of pyridine at room temperature (RT) for 1 h, and then a solution of 86 mg (0.675 mmol) of oxalyl chloride in 2 ml of dichloroethane is added. Subsequently, the mixture is stirred at 75° C. for 4 h. After cooling to RT, 0.5 ml of water is added. Then the mixture is stirred at RT for 30 min. The reaction solution is filtered and concentrated. The residue is purified by means of preparative HPLC (acetonitrile/water). Yield: 19 mg (8%).

후처리

  1. temperatureAfter cooling to RT
  2. stirringThen the mixture is stirred at RT for 30 min
  3. filtrationThe reaction solution is filtered
  4. concentrationconcentrated
  5. customThe residue is purified by means of preparative HPLC (acetonitrile/water)

출처 및 근거

ORD 기록
ord-89b8ed821e2b408fbdc7fc12a3897719
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09204650B2

반응 노트

불러오는 중…