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Formaldehyde → 2-(4-chloro-phenyl)-6-[3-methoxy-4-(1-methyl-azetidin-3-yloxy)-phenyl]-6H-thieno[2,3-c]pyridin-7-one

HRID 2384917
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HRID 2384917 반응식
F[C:2](F)(F)C(O)=O.[NH:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH:24]=[CH:23][C:22]4[CH:25]=[C:26]([C:28]5[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=5)[S:27][C:21]=4[C:20]3=[O:35])=[CH:15][C:14]=2[O:36][CH3:37])[CH2:9]1.CO.C=O.C([BH3-])#N.[Na+]>C(O)(=O)C>[Cl:34][C:31]1[CH:30]=[CH:29][C:28]([C:26]2[S:27][C:21]3[C:20](=[O:35])[N:19]([C:16]4[CH:17]=[CH:18][C:13]([O:12][CH:10]5[CH2:9][N:8]([CH3:2])[CH2:11]5)=[C:14]([O:36][CH3:37])[CH:15]=4)[CH:24]=[CH:23][C:22]=3[CH:25]=2)=[CH:33][CH:32]=1
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참가 물질

6

반응물 4

HCID 712FormaldehydeHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 689537536-[4-(Azetidin-3-yloxy)-3-methoxy-phenyl]-2-(4-chloro-phenyl)-6H-thieno[2,3-c]pyridin-7-one trifluoroacetate

생성물 1

HCID 248035822-(4-chloro-phenyl)-6-[3-methoxy-4-(1-methyl-azetidin-3-yloxy)-phenyl]-6H-thieno[2,3-c]pyridin-7-one수율 61.2%

시약·촉매·용매

1
HCID 176Acetic Acid용매

실험 절차

Mix 6-[4-(azetidin-3-yloxy)-3-methoxy-phenyl]-2-(4-chloro-phenyl)-6H-thieno[2,3-c]pyridin-7-one trifluoroacetic acid salt (210 mg, 0.48 mmol) with methanol (10 mL) and acetic acid (0.3 mL). Add a solution of formaldehyde (0.20 mL, 2.66 mmol, 37% aqueous solution) and stir the mixture for 15 min. Add sodium cyanoborohydride (110 mg, 1.75 mmol) and stir the mixture at RT overnight. Concentrate the mixture in vacuo and partition the crude material between saturated NaHCO3 (25 mL) and CH2Cl2 (25 mL). Remove the organic solution and extract the aqueous phase with additional CH2Cl2 (2×25 mL). Combine the organic solutions and concentrate in vacuo. Purify the crude material by flash chromatography, using 5% MeOH (2N NH3) in CH2Cl2 as eluent, to give 133 mg (61%) of 2-(4-chloro-phenyl)-6-[3-methoxy-4-(1-methyl-azetidin-3-yloxy)-phenyl]-6H-thieno[2,3-c]pyridin-7-one as a white solid.

후처리

  1. concentrationConcentrate the mixture in vacuo
  2. custompartition the crude material between saturated NaHCO3 (25 mL) and CH2Cl2 (25 mL)
  3. customRemove the organic solution
  4. extractionextract the aqueous phase with additional CH2Cl2 (2×25 mL)
  5. concentrationCombine the organic solutions and concentrate in vacuo
  6. customPurify the crude material by flash chromatography

출처 및 근거

ORD 기록
ord-1c89662f58194acc80138f80fe983c9a
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08263772B2

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