Pyrrolidine → HCID 68582157, compound

HRID 1035053Notes

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-65d43aca898a43c9b3383bb0e57fcff0
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546374B2

Reaction notes

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