Thionyl Chloride → HCID 58550614, 화합물

HRID 1890702노트

반응식

HRID 1890702 반응식
O[CH2:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]1[CH2:13][C@:14]3([CH2:24][C:8]=1[CH:7]=2)[C:22]1[C:17](=[N:18][CH:19]=[CH:20][CH:21]=1)[NH:16][C:15]3=[O:23].S(Cl)([Cl:27])=O>C(Cl)Cl>[Cl:27][CH2:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]1[CH2:13][C@:14]3([CH2:24][C:8]=1[CH:7]=2)[C:22]1[C:17](=[N:18][CH:19]=[CH:20][CH:21]=1)[NH:16][C:15]3=[O:23]

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 58550612(3′S)-6,8-Dihydro-3-(hydroxymethyl)spiro[7H-cyclopenta[g]quinoline-7,3′-[3H]pyrrolo[2,3-b]pyridin]-2′(1′H)-one

생성물 1

HCID 58550614HCID 58550614, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of (7S)-3-(hydroxymethyl)-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one from Step A (970 mg, 3.06 mmol) in CH2Cl2 (30 mL) was added thionyl chloride (2.23 mL, 30.1 mmol) and the resulting mixture was stirred at ambient temperature for 2 h, then concentrated in vacuo. The residue was partitioned between saturated aqueous NaHCO3 (30 mL) and CH2Cl2 (30 mL). The layers were separated and the aqueous layer was extracted further with CH2Cl2 (2×30 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to give the title. MS: m/z=336 (M+1).

후처리

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between saturated aqueous NaHCO3 (30 mL) and CH2Cl2 (30 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted further with CH2Cl2 (2×30 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give the title

출처 및 근거

ORD 기록
ord-4386b42c916040f3b571c5841e575b28
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507477B2

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