Dimethylamine → HCID 18512140, compound

HRID 1370855Notes

Reaction equation

HRID 1370855 reaction equation
[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH2:36][CH2:37][CH2:38]Br)[CH:30]=2)=[CH:24][CH:23]=1)[C:9]1[C:10]([CH3:20])=[C:11]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:40][NH:41][CH3:42]>C1COCC1>[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH2:36][CH2:37][CH2:38][N:41]([CH3:42])[CH3:40])[CH:30]=2)=[CH:24][CH:23]=1)[C:9]1[C:10]([CH3:20])=[C:11]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 18512211HCID 18512211, compound

Product 1

HCID 18512140HCID 18512140, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

The product from Example 72D in anhydrous THF (1 mL) was treated with 2.0 M dimethylamine (1.0 mL, 1.97 mmoles) in THF and heated to 70° C. overnight. Reaction mixture concentrated under reduced pressure and the residue was purified by preparative HPLC (CH3CN:0.1% trifluoroacetic acid in H2O) on a YMC ODS Guardpak column to provide the title compound. 1H NMR (300 MHz, CDCl3) δ7.10-7.30 (m, 11 H), 6.86 (d, 2 H), 6.72 (s, 1 H), 6.50-6.70 (m, 2 H), 6.32 (t, 1 H), 4.39 (s, 2 H), 4.35 (s, 2 H), 3.98 (t, 2 H), 3.30 (m, 2 H), 2.91 (s, 3 H), 2.90 (s, 3 H), 2.83 (s, 3 H), 2.25 (m, 2 H), 2.13 (s, 3 H); MS (ESI+) m/z 574 (M+H)+.

Workup

  1. customReaction mixture
  2. concentrationconcentrated under reduced pressure
  3. customthe residue was purified by preparative HPLC (CH3CN:0.1% trifluoroacetic acid in H2O) on a YMC ODS Guardpak column

Sources & evidence

ORD record
ord-809701f9b85f465cbd5bc59ba89dd422
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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