Hydrochloric Acid → tert-Butyl 2-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridine-2-carboxamido)ethylcarbamate

HRID 1711061ノート

反応式

HRID 1711061 の反応式
[F:1][C:2]1[CH:30]=[C:29]([N+:31]([O-])=O)[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]([NH:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:15])[S:13][C:6]=12.[BH4-].[Na+].Cl>CO.C1COCC1.Cl[Ni]Cl>[NH2:31][C:29]1[CH:28]=[CH:27][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[CH:11]=[C:12]([C:14]([NH:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:15])[S:13][C:6]=23)=[C:2]([F:1])[CH:30]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 59424685tert-Butyl 2-(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine-2-carboxamido)ethylcarbamate

生成物 1

HCID 59424551tert-Butyl 2-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridine-2-carboxamido)ethylcarbamate

試薬・触媒・溶媒 2

HCID 24385Nickel Dichloride触媒HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

To a solution of 292 (80 mg, 0.17 mmol) in MeOH/THF (1.7 mL/1.7 mL) at 0° C., was added NiCl2×6H2O (85 mg, 0.35 mmol), followed by addition of NaBH4 (26 mg, 0.68 mmol), portion wise. The reaction mixture was stirred for 15 min, treated with 2N aqueous HCl (2 mL), filtered; the filtrate was neutralized with aqueous NH4OH to pH 7 and partitioned between EtOAc and water. Organic phase was collected, dried over anhydrous Na2SO4 and concentrated. The residue (75 mg, quantitative yield, crude) was used directly in next step without further purification. MS (m/z): 447. 1 (M+H) (found).

後処理

  1. filtrationfiltered
  2. custompartitioned between EtOAc and water
  3. customOrganic phase was collected
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe residue (75 mg, quantitative yield, crude) was used directly in next step without further purification

出典と根拠

ORDレコード
ord-a24176584f4843f28400918e4bf7d79e
出典データセット
uspto-grants-2010_09
特許番号
US07790729B2

反応ノート

読み込み中…