Dimethylamine → HCID 54681969, compound

HRID 597834Notes

Reaction equation

HRID 597834 reaction equation
[F:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[N:17]([C:18](=[O:21])[C:19]=2[OH:20])[CH2:16][CH2:15][O:14][C:13]23[CH2:26][CH2:25][N:24]([C:27](=[O:32])[C:28]([O:30]C)=O)[CH2:23][CH2:22]2)=[O:9])=[C:4]([N:35]2[C:39]([CH3:40])=[N:38][CH:37]=[N:36]2)[CH:3]=1.[NH:41]([CH3:43])[CH3:42]>>[CH3:42][N:41]([CH3:43])[C:28](=[O:30])[C:27]([N:24]1[CH2:25][CH2:26][C:13]2([C:12]3=[N:11][C:10]([C:8]([NH:7][CH2:6][C:5]4[CH:33]=[CH:34][C:2]([F:1])=[CH:3][C:4]=4[N:35]4[C:39]([CH3:40])=[N:38][CH:37]=[N:36]4)=[O:9])=[C:19]([OH:20])[C:18](=[O:21])[N:17]3[CH2:16][CH2:15][O:14]2)[CH2:22][CH2:23]1)=[O:32]

Participants

3

Reactant 2

HCID 674DimethylamineHCID 54681968HCID 54681968, compound

Product 1

HCID 54681969HCID 54681969, compoundYield 36%

Procedure

A solution of Example 26 and 2M Me2NH/MeoH (2 mL, 4 mmol) was stirred for 18 h. at room temperature. Concentration gave an oil that was purified by chromatography (YMC Combiprep ODS-A, 30 mm×50 mm, MeOH/H2O/0.1% TFA) to give the title compound as white solid (0.227 g, 36%). 1H NMR (300 MHz, CDCl3) δ: 8.61 (1H, s), 8.34 (1H, t, J=5.3 Hz), 7.69 (1H, dd, J=8.6, 5.7 Hz), 7.27 (1H, td, J=8.1, 2.3 Hz), 7.01 (1H, dd, J=8.0, 2.2 Hz), 4.48-4.41 (2H, m), (4.18 (1H, dd, J=14.4, 5.3 Hz), 4.02 (4H, s), 3.64-3.59 (1H, m), 3.48-3.40 (1H, m), 3.09-3.04 (1H, m), 3.03 (3H, s), 3.00 (3H, s), 2.54 (3H, s), 2.39-2.29 (1H, m), 2.21-2.10 (1H, m), 1.99-1.88 (1H, m). HRMS (M+H) calcd for C26H30FN8O6: 569.2272; found: 569.2272.

Workup

  1. concentrationConcentration
  2. customgave an oil that
  3. customwas purified by chromatography (YMC Combiprep ODS-A, 30 mm×50 mm, MeOH/H2O/0.1% TFA)

Sources & evidence

ORD record
ord-c05ab8144cb948edaa69ab28b716767b
Source dataset
uspto-grants-2011_03
Patent number
US07897593B2

Reaction notes

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