Sodium Hydroxide → HCID 58015606, compound

HRID 1362999Notes

Reaction equation

HRID 1362999 reaction equation
[NH2:1][C:2]1[N:6]([C:7]([O:9]CC)=O)[N:5]=[C:4]2[C:12]([CH3:30])([CH3:29])[N:13]([C:15]([NH:17][C@@H:18]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:19][N:20]([CH3:22])[CH3:21])=[O:16])[CH2:14][C:3]=12.CCN(C(C)C)C(C)C.[Cl:40][C:41]1[C:46](C(Cl)=O)=[C:45]([F:50])[C:44]([CH3:51])=[CH:43][CH:42]=1.[OH-].[Na+]>>[Cl:40][C:41]1[C:46]([C:7]([NH:6][C:2]2[C:3]3[CH2:14][N:13]([C:15]([NH:17][C@@H:18]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:19][N:20]([CH3:21])[CH3:22])=[O:16])[C:12]([CH3:30])([CH3:29])[C:4]=3[NH:5][N:1]=2)=[O:9])=[C:45]([F:50])[C:44]([CH3:51])=[CH:43][CH:42]=1

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 27736716-Chloro-2-fluoro-3-methylbenzoyl chlorideHCID 58015674HCID 58015674, compound

Product 1

HCID 58015606HCID 58015606, compound

Procedure

To a 13×100 mm test tube were added one 3×6 mm stir bar, compound 71b, (0.1 M in CH2Cl2, 80 μmol, 1.0 eq), DIPEA solution (2 M in CH2Cl2, 160 μmol, 2.0 equiv), and 6-chloro-2-fluoro-3-methylbenzoyl chloride (0.1 M in CH2Cl2, 160 μmol, 2.0 eq.). The reaction was covered and stirred at RT for 12 h. NaOH (1M, 1000 μmol, 12.5 equiv) was added, and the reaction mixture was agitated for 15 minutes. After centrifugation, the top layer was removed. The organic layer was evaporated. MeOH (500 μL) and TEA (500 μL) were added, and the reaction mixture was allowed to stir at RT overnight. The solvents were evaporated, and the residue was reconstituted in DMSO. 1H NMR (500 MHz, D2O) d ppm 1.52 (s, 3H) 1.59 (s, 3H) 2.13 (s, 6H) 2.21 (s, 3H) 2.34 (dd, J=12.22, 5.63 Hz, 1H) 2.59 (dd, J=12.91, 10.16 Hz, 1H) 4.48 (d, J=11.81 Hz, 1H) 4.52 (d, J=12.09 Hz, 1H) 4.81 (q, J=5.77 Hz, 1H) 6.18 (br. s., 1H) 7.14 (t, J=7.55 Hz, 1H) 7.21-7.27 (m, 3H) 7.28-7.38 (m, 3H). LCMS: M+H+: 513.2

Workup

  1. additionTo a 13×100 mm test tube were added one 3×6 mm
  2. stirringstirred at RT for 12 h
  3. stirringthe reaction mixture was agitated for 15 minutes
  4. customAfter centrifugation, the top layer was removed
  5. customThe organic layer was evaporated
  6. additionMeOH (500 μL) and TEA (500 μL) were added
  7. stirringto stir at RT overnight
  8. customThe solvents were evaporated

Sources & evidence

ORD record
ord-8cc83535edda4c66990f4f023e714bf8
Source dataset
uspto-grants-2011_02
Patent number
US07884117B2

Reaction notes

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