2-(Trifluoromethyl)phenylhydrazine → HCID 57504514, 화합물

HRID 1098161

반응식

HRID 1098161 반응식
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][NH2:10].[O:13]([C:20]1[C:25]([CH:26]=O)=[C:24](OC2C=CC=CC=2)[N:23]=[CH:22][N:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CCN(P1(N(C)CCCN1)=NC(C)(C)C)CC>C1COCC1>[O:13]([C:20]1[N:21]=[CH:22][N:23]=[C:24]2[N:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:2]([F:11])([F:12])[F:1])[N:10]=[CH:26][C:25]=12)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

참가 물질

5

반응물 3

HCID 5208002-(Trifluoromethyl)phenylhydrazineHCID 199900182-tert-butylimino-N,N-diethyl-1-methyl-1,3,2lambda5-diazaphosphinan-2-amineHCID 574386554,6-Diphenoxypyrimidine-5-carbaldehyde

생성물 1

HCID 57504514HCID 57504514, 화합물수율 42.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(2-(trifluoromethyl)phenyl)hydrazine (CAS no. 365-34-4) (102 mg, 0.58 mmol) was added to 4,6-diphenoxypyrimidine-5-carbaldehyde (Intermediate Z2) (169 mg, 0.58 mmol) in THF (2 mL) the resulting solution was stirred at room temperature for 5 minutes. 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine on polystyrene (526 mg, 1.16 mmol) was added and sealed into a microwave tube. The reaction was heated to 150° C. for 10 hours in a microwave reactor and cooled to RT. The reaction mixture was filtered and evaporated to dryness. The crude product was purified by flash silica chromatography, eluting with 10 to 80% ethyl acetate in isohexane to afford the product (88 mg, 42.7%). 1H NMR (400 MHz, CDCl3) δ 7.29-7.33 (2H, m), 7.34-7.39 (1H, m), 7.49-7.58 (3H, m), 7.67-7.71 (1H, m), 7.74-7.78 (1H, m), 7.90-7.92 (1H, m), 8.08 (1H, s), 8.56 (1H, s); m/z (ES+) (M+H)+=357; HPLC tR=2.66 min.

후처리

  1. customsealed into a microwave tube
  2. temperatureThe reaction was heated to 150° C. for 10 hours in a microwave reactor
  3. temperaturecooled to RT
  4. filtrationThe reaction mixture was filtered
  5. customevaporated to dryness
  6. customThe crude product was purified by flash silica chromatography
  7. washeluting with 10 to 80% ethyl acetate in isohexane

출처 및 근거

ORD 기록
ord-e1a964ae487e4f749ff07b45aea31f7a
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143263B2

연결된 노트

불러오는 중…