Cyclopropylamine → HCID 68452319, compound

HRID 2357651Notes

Reaction equation

HRID 2357651 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.CC[N:28]([CH:32]([CH3:34])[CH3:33])C(C)C.C1(N)CC1>S(Cl)(Cl)=O.C(OCC)(=O)C>[CH:32]1([NH:28][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 the mixture was heated to 65° C. for 1 h. The reaction mixture was concentrated in vacuo and azeotropically dried with toluene, then dissolved/suspended in THF 99.9% (3.1 mL) and DIPEA (216 μl, 1238 μmol) and cyclopropylamine (71 μl, 1238 μmol) were added. The mixture was stirred at RT for 2 h, then diluted with 50 mL ethyl acetate and partitioned with sodium bicarbonate (saturated, aqueous). The organics were washed 2×50 mL with sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, and concentrated in vacuo to give crude yellow product, which was purified by chromatography to afford the title compound. MS (ES+): 395(M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dry with materialazeotropically dried with toluene
  3. custompartitioned with sodium bicarbonate (saturated, aqueous)
  4. washThe organics were washed 2×50 mL with sodium bicarbonate (saturated, aqueous)
  5. customseparated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto give crude yellow product, which
  9. customwas purified by chromatography

Sources & evidence

ORD record
ord-468cd13f330048169d6077ad24bde8bc
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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