Acetic Acid → HCID 56597208, compound

HRID 1505465Notes

Reaction equation

HRID 1505465 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2([C:11](OCC)=[O:12])[CH2:10][CH2:9]2)=[CH:6][N:5]=[C:4]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=3[F:33])[N:17]=2)[N:3]=1.CC(C)([O-])C.[K+].O.C(O)(=O)C>C1COCC1>[F:33][C:27]1[CH:28]=[C:29]([F:32])[CH:30]=[CH:31][C:26]=1[CH2:25][N:18]1[C:19]2=[N:20][CH:21]=[CH:22][CH:23]=[C:24]2[C:16]([C:4]2[N:5]=[CH:6][C:7]3[C:8]4([CH2:9][CH2:10]4)[C:11](=[O:12])[NH:1][C:2]=3[N:3]=2)=[N:17]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 23665647Potassium tert-butoxideHCID 117702922HCID 117702922, compound

Product 1

HCID 56597208HCID 56597208, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The intermediate from Step b) was taken up in 20 ml of THF, 109 mg (0.974 mmol) of potassium tert-butoxide were added under an atmosphere of argon and the mixture was stirred at RT for 2 h. Water was added, and the pH of the reaction mixture was adjusted to pH=5 with acetic acid. The mixture was stirred at RT for 10 min and the mixture was extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated on a rotary evaporator. The residue was purified by preparative HPLC (mobile phase:acetonitrile/water with 0.1% formic acid, gradient 50:50→70:30). This gave 101 mg of the title compound (25% of theory).

Workup

  1. stirringThe mixture was stirred at RT for 10 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. concentrationconcentrated on a rotary evaporator
  5. customThe residue was purified by preparative HPLC (mobile phase:acetonitrile/water with 0.1% formic acid, gradient 50:50→70:30)

Sources & evidence

ORD record
ord-b968deeec3bc49f987b57d57a05f9d4b
Source dataset
uspto-grants-2015_12
Patent number
US09216978B2

Reaction notes

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