Sodium Hydroxide → 3,5-Diamino-6-chloro-pyrazine-2-carboxylic acid {(S)-2-[3-(4-methoxy-phenyl)-propylamino]-pentyl}-amide hydrochloride

HRID 1183025노트

반응식

HRID 1183025 반응식
Cl.[NH2:2][C@@H:3]([CH2:17][CH2:18][CH3:19])[CH2:4][NH:5][C:6]([C:8]1[C:13]([NH2:14])=[N:12][C:11]([NH2:15])=[C:10]([Cl:16])[N:9]=1)=[O:7].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH:30]=O)=[CH:24][CH:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(Cl)Cl>[ClH:16].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30][NH:2][C@@H:3]([CH2:17][CH2:18][CH3:19])[CH2:4][NH:5][C:6]([C:8]2[C:13]([NH2:14])=[N:12][C:11]([NH2:15])=[C:10]([Cl:16])[N:9]=2)=[O:7])=[CH:24][CH:23]=1

참가 물질

6

반응물 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 111266073-(4-Methoxyphenyl)propanalHCID 866518883,5-Diamino-6-chloro-pyrazine-2-carboxylic acid ((S)-2-amino-pentyl)-amide hydrochloride

생성물 1

HCID 866518933,5-Diamino-6-chloro-pyrazine-2-carboxylic acid {(S)-2-[3-(4-methoxy-phenyl)-propylamino]-pentyl}-amide hydrochloride

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 3,5-Diamino-6-chloro-pyrazine-2-carboxylic acid ((S)-2-amino-pentyl)-amide hydrochloride (Example 4) (400 mg, 1.467 mmol), 3-(4-methoxyphenyl)propionaldehyde (181 mg, 1.103 mmol) and sodium triacetoxyborohydride (467 mg, 2.205 mmol) in DCM (150 mL) is heated at reflux overnight. The reaction mixture is allowed to cool, and 1 N NaOH solution (50 mL) and DCM (50 mL) are added. The organic phase is separated and the aqueous phase is extracted once with DCM. The combined organic phases are washed with sat. aq. NaCl solution, dried (MgSO4), and concentrated in vacuo to afford a yellow solid. Purification by flash column chromatography (SiO2, MeOH:DCM, gradient 2-10%+0.1% TEA) affords the title compound. [M+H]+ 421. 1H NMR (400 MHz, CDCl3) δ 8.69 (2H, br), 8.23 (1H, t), 7.25 (4H, br), 7.11 (2H, d), 6.84 (2H, d), 3.72 (3H, s), 3.55-3.45 (2H, m), 3.25-3.15 (1H, m), 3.03-2.92 (2H, m), 2.58 (2H, t), 1.85-1.73 (2H, m), 1.65-1.27 (4H, m), 0.89 (3H, t).

후처리

  1. temperatureat reflux overnight
  2. temperatureto cool
  3. customThe organic phase is separated
  4. extractionthe aqueous phase is extracted once with DCM
  5. washThe combined organic phases are washed with sat. aq. NaCl solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto afford a yellow solid
  9. customPurification by flash column chromatography (SiO2, MeOH:DCM, gradient 2-10%+0.1% TEA)

출처 및 근거

ORD 기록
ord-39fbad91bee14dbb8805ec8c09d0f02c
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664228B2

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