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

HRID 500913노트

반응식

HRID 500913 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 24385Nickel Dichloride촉매HCID 21899815MeOH tetrahydrofuran용매

실험 절차

To a solution of 292 (80mg, 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).

후처리

  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

출처 및 근거

ORD 기록
ord-9662157bc8d94486a8a0a423b19e814f
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772247B2

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