Cyclopropylamine → HCID 68452319, compound

HRID 2357599Notes

Reaction equation

HRID 2357599 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:23]([OH:25])=O)[S:5][C:6]=1[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[N:12][N:11]=[CH:10]2.C([N:29]([CH:32]([CH3:34])[CH3:33])CC)(C)C.C1(N)CC1>S(Cl)(Cl)=O.CCOC(C)=O>[CH:32]1([NH:29][C:23]([C:4]2[S:5][C:6]([C:7]3[CH:8]=[C:9]4[C:14](=[CH:15][CH:16]=3)[C:13]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[N:12][N:11]=[CH:10]4)=[C:2]([CH3:1])[CH:3]=2)=[O:25])[CH2:34][CH2:33]1

Participants

6

Reactant 3

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 68452315HCID 68452315, compound

Product 1

HCID 68452319HCID 68452319, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
65 °C

Procedure

4-Methyl-5-(1-morpholinophthalazin-6-yl)thiophene-2-carboxylic acid (140 mg, 309 μmol) was suspended in thionyl chloride (3.1 mL) and heated to 65° C. for 1 h. The reaction mixture was concentrated in vacuo and azeotropically dried with toluene, before being dissolved/suspended in tetrahydrofuran 99.9% (3.1 mL), diisopropylethylamine (216 μl, 1238 μmol) and cyclopropylamine (71 μl, 1238 μmol). The reaction was stirred at RT for 2 h, diluted with 50 mL of EtOAc, added to an addition funnel and partitioned with sodium bicarbonate (saturated, aqueous). The organic layer was washed 2 times with 50 mL of sodium bicarbonate (saturated, aqueous), dried over sodium sulfate, and concentrated via rotovap to give a crude yellow product. The crude was purified by chromatography, to obtain the title compound. Found MS (ES+): 395(M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dry with materialazeotropically dried with toluene
  3. additionadded to an addition funnel
  4. custompartitioned with sodium bicarbonate (saturated, aqueous)
  5. washThe organic layer was washed 2 times with 50 mL of sodium bicarbonate (saturated, aqueous)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated via rotovap
  8. customto give a crude yellow product
  9. customThe crude was purified by chromatography

Sources & evidence

ORD record
ord-54a424aaf59b47b59cec111c54b8f408
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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