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Sodium borohydride → 8-tert-Butyl-4-(2-hydroxymethyl-3-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-phenyl)-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-one

HRID 1879685
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HRID 1879685 반응식
[C:1]([C:5]1[CH:47]=[CH:46][C:8]2[C:9](=[O:45])[N:10]([C:14]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]4[CH:27]=[C:26]([NH:28][C:29]5[CH:34]=[CH:33][C:32]([C:35]([N:37]6[CH2:42][CH2:41][O:40][CH2:39][CH2:38]6)=[O:36])=[CH:31][N:30]=5)[C:25](=[O:43])[N:24]([CH3:44])[CH:23]=4)[C:15]=3[CH:16]=[O:17])[CH2:11][CH2:12][O:13][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)(C)C.C1COCC1>[C:1]([C:5]1[CH:47]=[CH:46][C:8]2[C:9](=[O:45])[N:10]([C:14]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]4[CH:27]=[C:26]([NH:28][C:29]5[CH:34]=[CH:33][C:32]([C:35]([N:37]6[CH2:42][CH2:41][O:40][CH2:39][CH2:38]6)=[O:36])=[CH:31][N:30]=5)[C:25](=[O:43])[N:24]([CH3:44])[CH:23]=4)[C:15]=3[CH2:16][OH:17])[CH2:11][CH2:12][O:13][C:7]=2[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]
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참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 595485232-(8-tert-Butyl-5-oxo-2,3-dihydro-5H-benzo[f][1,4]oxazepin-4-yl)-6-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-benzaldehyde

생성물 1

HCID 469451838-tert-Butyl-4-(2-hydroxymethyl-3-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-phenyl)-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-one수율 54.6%

시약·촉매·용매 2

HCID 3776
Isopropanol
용매
HCID 8028Tetrahydrofuran용매

실험 절차

To 2-(8-tert-Butyl-5-oxo-2,3-dihydro-5H-benzo[f][1,4]oxazepin-4-yl)-6-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-benzaldehyde (0.27 mmol) in isopropanol (5 mL) and THF (10 mL) at 0 C with stirring was added sodium borohydride (21 mg, 2 eq) and then the ice bath was removed and the resulting mixture was stirred at room temperature for 45 minutes. TLC analysis indicated that the reaction was complete so the mixture was diluted with ethyl acetate (150 mL) and water (50 mL). The layers were partitioned, then separated and the organic layer was further washed with water (3×50 mL) and then finally washed with brine ((1×50 mL). The ethyl acetate layer was dried over magnesium sulfate, filtered and concentrated. Purification by Thin Layer Chromatography on silica gel eluting with 10% methanol in dichloromethane afforded the title compound as a light grey powder (94 mg), (M+H)+=638.

후처리

  1. customthe ice bath was removed
  2. additionwas diluted with ethyl acetate (150 mL) and water (50 mL)
  3. customThe layers were partitioned
  4. customseparated
  5. washthe organic layer was further washed with water (3×50 mL)
  6. washfinally washed with brine ((1×50 mL)
  7. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by Thin Layer Chromatography on silica gel eluting with 10% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-6af2d96a5e8f4c0898b653942ae0ddcf
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08318719B2

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