Dimethylamine → HCID 67040627, compound

HRID 605150Notes

Reaction equation

HRID 605150 reaction equation
ClC(Cl)(Cl)CO[C:5](=[O:45])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:30])[NH:21][C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[C:24]([F:29])[CH:23]=3)=[CH:16][C:15]=2[NH:31][C:32]2[C:33]3[CH:41]=[CH:40][C:39]([CH:42]([CH3:44])[CH3:43])=[N:38][C:34]=3[N:35]=[CH:36][N:37]=2)=[CH:9][CH:8]=1.C1CCN2[C:51](=[N:52][CH2:53]CC2)CC1.CNC>O1CCCC1>[CH3:51][N:52]([CH3:53])[C:5](=[O:45])[NH:6][C:7]1[CH:8]=[CH:9][C:10]([S:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[C:24]([F:29])[CH:23]=3)=[O:30])=[CH:16][C:15]=2[NH:31][C:32]2[C:33]3[CH:41]=[CH:40][C:39]([CH:42]([CH3:44])[CH3:43])=[N:38][C:34]=3[N:35]=[CH:36][N:37]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 67040154HCID 67040154, compound

Product 1

HCID 67040627HCID 67040627, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

The product of Example 105B (0.108 g, 0.15 mmol) in tetrahydrofuran (3 mL) was treated with DBU (0.023 g, 0.15 mmol) and Dimethylamine (2.0 M in THF, 0.75 mL, 1.5 mmol) and heated at 60° C. for 20 minutes in a sealed tube, cooled, and concentrated under vacuum. The resulting residue was purified by chromatography on silica eluting with 97:3 dichloromethane/methanol to provide the title compound (0.08 g, 88%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.34 (d, J=6.99 Hz, 6 H), 2.19 (s, 3 H), 2.93 (s, 6 H), 3.15-3.29 (m, 1 H), 7.01 (d, J=8.46 Hz, 1 H), 7.23 (t, J=8.64 Hz, 1 H), 7.33 (d, J=8.46 Hz, 2 H), 7.43 (dd, J=8.27, 1.65 Hz, 1 H), 7.57 (d, J=8.82 Hz, 2 H), 7.62-7.71 (m, 2 H), 7.80 (dd, J=8.27, 1.65 Hz, 1 H), 7.99 (s, 1 H), 8.50 (s, 1 H), 8.60 (s, 1 H), 8.87 (d, J=8.46 Hz, 1 H), 10.22 (s, 1 H), 10.30 (s, 1 H); MS (ESI+) m/z 610 (M+H)+.

Workup

  1. temperaturecooled
  2. concentrationconcentrated under vacuum
  3. customThe resulting residue was purified by chromatography on silica eluting with 97:3 dichloromethane/methanol

Sources & evidence

ORD record
ord-84cf6e342d1b4793bd529520f0ae8e20
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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