Acetic Acid → Formate

HRID 82092

반응식

HRID 82092 반응식
Cl.[NH:2]1[CH2:5][CH2:4][CH2:3]1.[CH:6]([C:8]1[CH:9]=[C:10]([CH2:14][C:15]([NH:17][C:18]2[CH:19]=[N:20][CH:21]=[C:22]([C:24]([C:26]3[C:34]4[CH:33]=[N:32][CH:31]=[N:30][C:29]=4[N:28]([CH:35]([CH3:37])[CH3:36])[CH:27]=3)=[O:25])[CH:23]=2)=[O:16])[CH:11]=[CH:12][CH:13]=1)=O.[C:38]([OH:41])(=[O:40])C.[C:42]([O:45][BH-](OC(=O)C)OC(=O)C)(=[O:44])C.[Na+]>C(Cl)Cl.O>[CH:38]([OH:41])=[O:40].[N:2]1([CH2:6][C:8]2[CH:9]=[C:10]([CH2:14][C:15]([NH:17][C:18]3[CH:19]=[N:20][CH:21]=[C:22]([C:24]([C:26]4[C:34]5[CH:33]=[N:32][CH:31]=[N:30][C:29]=5[N:28]([CH:35]([CH3:37])[CH3:36])[CH:27]=4)=[O:25])[CH:23]=3)=[O:16])[CH:11]=[CH:12][CH:13]=2)[CH2:5][CH2:4][CH2:3]1.[CH:42]([O-:45])=[O:44]

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 12308726Azetidine hydrochlorideHCID 866720722-(3-formylphenyl)-N-{5-[(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)carbonyl]pyridin-3-yl}acetamide

생성물 2

HCID 283FormateHCID 708172772-[3-(azetidin-1-ylmethyl)phenyl]-N-{5-[(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)carbonyl]pyridin-3-yl}acetamide formate salt

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

Azetidine hydrochloride (10 mg, 0.11 mmol) was added to a stirred solution of 2-(3-formylphenyl)-N-{5-[(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)carbonyl]pyridin-3-yl}acetamide (Preparation 192, 23 mg, 0.05 mmol) in DCM (1 mL) and acetic acid (0.04 mL, 0.60 mmol). The reaction mixture was stirred for 30 min at room temperature before addition of sodium triacetoxyborohydride (29 mg, 0.14 mmol) and stirring continued for 3 hours. Water (1 mL) was added and the mixture concentrated in vacuo (with toluene azeotroping). The residue was purified by preparative HPLC to afford the title compound as a formate salt in 12% yield, 3.4 mg.

후처리

  1. concentrationthe mixture concentrated in vacuo (with toluene azeotroping)
  2. customThe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-d2d80c6da06f4393a1275495ee8ff960
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846698B2

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