Acetic Acid → Formate

HRID 82092

反応式

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]

参加物

実験手順

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.

後処理

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

出典と根拠

ORDレコード: ord-d2d80c6da06f4393a1275495ee8ff960
出典データセット: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08846698B2

反応式

参加物

反応物 4

生成物 2

試薬・触媒・溶媒 2

実験手順

後処理

出典と根拠

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