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

HRID 1592651ノート

反応式

HRID 1592651 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7253e7e006bd4a2b944497fac71326d6
出典データセット
uspto-grants-2007_11
特許番号
US07291631B2

反応ノート

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