Isopropanol → HCID 25116906, compound

HRID 2077067Notes

Reaction equation

HRID 2077067 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:15]=[C:14]([NH:16][CH2:17][C:18]3[C:19]([N:24]([CH3:29])[S:25]([CH3:28])(=[O:27])=[O:26])=[N:20][CH:21]=[CH:22][CH:23]=3)[C:13]([C:30]([F:33])([F:32])[F:31])=[CH:12][N:11]=2)=[CH:5][CH:4]=1.[NH2:34][CH:35]([CH2:38][OH:39])[CH2:36][OH:37].[OH-].[Na+].CC(O)C>C(Cl)Cl>[OH:37][CH2:36][CH:35]([NH:34][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:15]=[C:14]([NH:16][CH2:17][C:18]3[C:19]([N:24]([CH3:29])[S:25]([CH3:28])(=[O:27])=[O:26])=[N:20][CH:21]=[CH:22][CH:23]=3)[C:13]([C:30]([F:33])([F:32])[F:31])=[CH:12][N:11]=2)=[CH:5][CH:4]=1)[CH2:38][OH:39]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 68294SerinolHCID 25116905HCID 25116905, compound

Product 1

HCID 25116906HCID 25116906, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 7 (100 mg, 0.200 mmol), 2-amino-1,3-propanediol (90.9 mg, 0.998 mmol), sodium hydroxide (7.98 mg, 0.200 mmol) and 2-propanol (0.5 mL) was heated to reflux. After 30 minutes the mixture was cooled, treated with DCM, and washed with water. The organic phase was dried over MgSO4, filtered and concentrated. The resultant residue was then purified by column chromatography (silica gel; eluting with 6% MeOH/DCM with NH4OH), and the eluents containing the product were combined and concentrated to provide 8 as a white solid. Yield: 60.9 mg, 55%. MS+ 556.2. 1H NMR (500 MHz, d6-DMSO) δ: 9.48 (s, 1H), 8.41 (s, 1H), 8.21 (s, 1H), 7.59 (m, 2H), 7.34 (m, 3H), 6.99 (d, 2H), 4.75 (d, 2H), 4.35 (t, 2H), 3.58 (s, 2H), 3.34 (m, 4H), 3.12 (s, 3H), 3.09 (s, 3H), 2.45 (m, 1H). FAK IC50: <0.000595 μM (Table 1, Example 389)

Workup

  1. temperaturewas heated to reflux
  2. temperatureAfter 30 minutes the mixture was cooled
  3. washwashed with water
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resultant residue was then purified by column chromatography (silica gel; eluting with 6% MeOH/DCM with NH4OH)
  8. additionthe eluents containing the product
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0cbd0ba5859f4cac8039a41ddc666821
Source dataset
uspto-grants-2011_04
Patent number
US07928109B2

Reaction notes

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