Acetic Anhydride → HCID 58997215, compound

HRID 1592670Notes

Reaction equation

HRID 1592670 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:10][N:11]([CH2:21][C:22]2[C:27]([CH3:28])=[CH:26][C:25]([Cl:29])=[CH:24][N:23]=2)[C:12]([CH3:20])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH3:13])=[C:7]([CH3:9])[CH:8]=1.[CH3:30][C:31](OC(C)=O)=[O:32].CCN(CC)CC.C([O-])(O)=[O:45].[Na+]>C(Cl)Cl>[Cl:29][C:25]1[CH:26]=[C:27]([CH3:28])[C:22]([CH2:21][N:11]([CH2:10][C:6]2[CH:5]=[CH:4][C:3]([CH2:2][NH:1][C:31](=[O:32])[CH3:30])=[CH:8][C:7]=2[CH2:9][OH:45])[C:12]([CH3:20])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH3:13])=[N:23][CH:24]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 67271946HCID 67271946, compound

Product 1

HCID 58997215HCID 58997215, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-aminomethyl-2-{[(5-chloro-3-methyl-pyridin-2-ylmethyl)-(1-methyl-1-pyridin-2-yl-ethyl)-amino]-methyl}-phenyl)-methane (0.0966 g, 0.23 mmol) in CH2Cl2 (3 mL) was added Ac2O (0.0213 mL, 0.23 mmol), Et3N (0.05 mL, 0.35 mmol), and KI (0.0038 g, 0.02 mmol), and stirred for 18 hours at room temperature. Saturated NaHCO3 (10 mL) was added and extracted with CH2Cl2 (3×20 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated. Purification of the crude material by column chromatography on silica gel (100:1:1 CH2Cl2-MeOH—NH4OH) provided 0.0573 g (52%) of COMPOUND 403 as a white solid. 1H NMR (CDCl3) δ 1.61 (s, 6H), 2.00 (s, 3H), 2.08 (s, 3H), 3.69 (s, 2H), 3.90 (s, 2H), 4.30 (d, 2H, J=5.4 Hz), 4.53 (s, 2H), 5.65 (s, 1H), 6.69 (s, 1H), 6.94 (d, 1H, J=7.5 Hz), 7.03-7.09 (m, 3H), 7.17 (s, 1H), 7.54 (t, 1H, J=7.8 Hz), 7.75 (d, 1H, J=8.1 Hz), 8.04 (s, 1H), 8.47 (d, 1H, J=6.0 Hz). 13C NMR (CDCl3) δ 18.72, 23.66, 24.47, 43.62, 51.37, 53.92, 63.30, 64.75, 122.16, 122.99, 127.27, 129.31, 130.85, 131.46, 132.38, 136.22, 137.30, 138.04, 138.13, 141.45, 144.53, 147.99, 156.81, 165.70, 170.29. ES-MS m/z 467.2 (M+H). Anal. Calcd. for C26H31N4ClO2.0.1CH2Cl2.0.4H2O: C, 64.94; H, 6.68; N, 11.61; Cl, 8.81. Found: C, 64.69; H, 6.58; N, 11.37; Cl, 9.18.

Workup

  1. extractionextracted with CH2Cl2 (3×20 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the crude material by column chromatography on silica gel (100:1:1 CH2Cl2-MeOH—NH4OH)

Sources & evidence

ORD record
ord-06a0ed2345fb42dd96453bf7fbc920e5
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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