Pyrrolidine → HCID 68582157, compound

HRID 645605Notes

Reaction equation

[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18](F)[CH:17]=2)=[N:12][N:11]=[N:10]1.[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>O1CCCC1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:17]=2)=[N:12][N:11]=[N:10]1

Participants

Conditions

Temperature: 60 °C

Procedure

To an oven-dried N2-purged, 20-mL scintillation vial containing a magnetic stir bar was added the product of Example 143C (34 mg, 0.10 mmol) and anhydrous tetrahydrofuran (1 mL). Neat pyrrolidine (160 mL, 140 mg, 2.0 mmol) was added via syringe, and the vial was sealed. The reaction mixture was heated to 60° C. and the vial was shaken for 48 hours. After cooling to room temperature, the solvent/volatiles were removed by rotary evaporator to give a brown oil. The product was purified by flash chromatography (silica gel: 25% ethyl acetate, 75% hexanes—product Rf˜0.2) to give 5.6 mg (14%) of the title compound as a white powder. MS (ESI+) m/z 390.1 (M+H)+; 1H NMR (DMSO-d6) δ 1.54 (br s, 4H), 3.46 (br s, 4H), 4.61 (d, J=6.1 Hz, 2H), 6.37 (br s, 1H), 6.46-6.48 (m, 1H), 7.39-7.47 (m, 2H), 7.72 (dd, J=7.6, 2.2 Hz, 1H), 8.08 (d, J=5.1 Hz, J=5.1 Hz, 1H).

Workup

customTo an oven-dried N2-purged
addition20-mL scintillation vial containing a magnetic stir bar
customthe vial was sealed
temperatureAfter cooling to room temperature
customthe solvent/volatiles were removed by rotary evaporator
customto give a brown oil
customThe product was purified by flash chromatography (silica gel: 25% ethyl acetate, 75% hexanes—product Rf˜0.2)

Sources & evidence

ORD record: ord-edc1caae56ba49488e08b9af5f8801e4
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07704997B1

Reaction notes

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