Cyanogen Bromide → 5-(8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-4-(2-chlorophenyl)-4H-1,2,4-triazol-3-amine

HRID 2078942노트

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HRID 2078942 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15](=[N:24][NH2:25])[NH:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[Cl:23])=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:26]=1.[N:27]#[C:28]Br>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15]4[N:16]([C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=5[Cl:23])[C:28]([NH2:27])=[N:25][N:24]=4)=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:26]=1

참가 물질

4

반응물 2

HCID 10476Cyanogen BromideHCID 178514378HCID 178514378, 화합물

생성물 1

HCID 579002025-(8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-4-(2-chlorophenyl)-4H-1,2,4-triazol-3-amine수율 21%

시약·촉매·용매 1

HCID 887Methanol용매2회

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온도
45 °C

실험 절차

A solution of crude 8-bromo-N-(2-chlorophenyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carbohydrazonamide (195, 0.434) in methanol (5 mL) was treated with a solution of cyanogen bromide (115 mg, 1.1 mmol) in methanol (1 mL) at room temperature. The reaction vessel was sealed and heated at 45° C. for 2 h, cooled to room temperature, quenched upon addition of saturated sodium bicarbonate and extracted with ethylacetate. The combined organics were dried over sodium sulfate and concentrated and the residue purified by flash column chromatography (1-10% MeOH in methylene chloride to give 287 (43 mg, 21% yield). MS (ESI): 475.0

후처리

  1. customThe reaction vessel was sealed
  2. temperaturecooled to room temperature
  3. customquenched upon addition of saturated sodium bicarbonate
  4. extractionextracted with ethylacetate
  5. dry with materialThe combined organics were dried over sodium sulfate
  6. concentrationconcentrated
  7. customthe residue purified by flash column chromatography (1-10% MeOH in methylene chloride

출처 및 근거

ORD 기록
ord-8a78d7718d9a4c4699f934a38316c69c
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928248B2

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