Water → N-(4-{[bis-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-3-hydroxymethyl-benzyl)-methanesulfonamide

HRID 1592651노트

반응식

HRID 1592651 반응식
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([CH2:10][NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:7]=[CH:6][C:5]=1[CH2:16][N:17]([CH2:26][C:27]1[C:32]([CH3:33])=[CH:31][CH:30]=[CH:29][N:28]=1)[CH2:18][C:19]1[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][N:20]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[CH3:33][C:32]1[C:27]([CH2:26][N:17]([CH2:16][C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:9][C:4]=2[CH2:3][OH:2])[CH2:18][C:19]2[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][N:20]=2)=[N:28][CH:29]=[CH:30][CH:31]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 672728122-{[Bis-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-5-(methanesulfonylamino-methyl)-benzoic acid methyl ester

생성물 1

HCID 58997093N-(4-{[bis-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-3-hydroxymethyl-benzyl)-methanesulfonamide수율 81%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Under N2, To a solution of 2-{[bis-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-5-(methanesulfonylamino-methyl)-benzoic acid methyl ester (0.217 g, 0.450 mmol) in THF (20 mL) was added LiAlH4 (1.0 M in THF, 0.67 mL, 0.67 mmol) at −78° C. After the addition the reaction mixture was brought to room temperature and stirred at room temperature for 30 min. H2O (10 mL) was added, and THF removed. The aqueous residue was extracted with CH2Cl2 (3×20 mL), and the extracts were combined and dried over Na2SO4. After filtration the solvent was removed, and the residue was purified on silica gel column (500:25:1 CH2Cl2/MeOH/NH4OH), affording a white foam (0.165 g, 81%). 1H NMR (CDCl3) δ 2.13 (s, 6H), 2.87 (s, 3H), 3.71 (s, 4H), 3.90 (s, 2H), 4.25 (s, br, 2H), 4.28 (d, 2H, J=6.0 Hz), 4.59 (t, 1H, J=60 Hz), 6.65 (s, br, 1H), 7.06 (dd, 2H, J=4.8, 7.8 Hz), 7.21 (dd, 1H, J=1.5, 7.8 Hz), 7.26-7.31 (m, 2H), 7.38 (d, 2H, J=7.8 Hz), 8.35 (d, 2H, J=4.8 Hz); 13C NMR (CDCl3) δ 18.26, 41.00, 46.84, 57.30, 58.68, 62.79, 122.60, 127.04, 130.68, 131.99, 133.12, 136.72, 137.03, 138.30, 142.35, 146.18, 155.87. ES-MS m/z 455 (M+H). Anal. Calcd. for C24H30N4O3S.0.21CH2Cl2: C, 61.55; H, 6.49; N, 11.86; S, 6.79. Found: C, 61.62; H, 6.58; N, 11.64; S, 6.77.

후처리

  1. additionAfter the addition the reaction mixture
  2. customwas brought to room temperature
  3. customTHF removed
  4. extractionThe aqueous residue was extracted with CH2Cl2 (3×20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration the solvent
  7. customwas removed
  8. customthe residue was purified on silica gel column (500:25:1 CH2Cl2/MeOH/NH4OH)

출처 및 근거

ORD 기록
ord-7253e7e006bd4a2b944497fac71326d6
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07291631B2

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