2-(Pyrrolidin-1-ylmethyl)pyrrolidine → HCID 66558240, compound

HRID 1530486Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][N:15]=1)[C:12]1[N:8]([CH:9]=[C:10]([C:16]3[N:20]([CH:21]([CH3:23])[CH3:22])[N:19]=[CH:18][N:17]=3)[N:11]=1)[CH2:7][CH2:6][O:5]2.[CH2:24]([N:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1)[CH:25]1[CH2:29][CH2:28][CH2:27][NH:26]1>CN1C(=O)CCC1>[CH:21]([N:20]1[C:16]([C:10]2[N:11]=[C:12]3[C:13]4[CH:14]=[N:15][C:2]([N:26]5[CH2:27][CH2:28][CH2:29][CH:25]5[CH2:24][N:30]5[CH2:34][CH2:33][CH2:32][CH2:31]5)=[CH:3][C:4]=4[O:5][CH2:6][CH2:7][N:8]3[CH:9]=2)=[N:17][CH:18]=[N:19]1)([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 12-chloro-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6,13-triazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene from Example 135 (150 mg, 0.454 mmol), TEA (0.500 mL), and 1,2′-methylenedipyrrolidine (420 mg, 2.73 mmol) in NMP (0.500 mL) was stirred at 150° C. for 24 hr under nitrogen atmosphere. The resultant mixture was purified by reverse phase combiflash eluting with 0-50% gradient of CH3CN in 0.5% NH4HCO3 to afford 105 (81 mg, 40% yield) as white solid. LCMS (ESI): RT=4.54 min, m/z: 449.3 [M+H+]. 1H-NMR (500 MHz, DMSO-d6): δ 9.09 (s, 1H), 7.89 (s, 1H), 7.83 (s, 1H), 5.98-5.93 (m, 2H), 4.52-4.47 (m, 4H), 4.14 (s, 1H), 3.47 (s, 1H), 3.27 (s, 1H), 2.58-2.56 (m, 2H), 2.50-2.46 (m, 4H), 2.06-1.93 (m, 2H), 1.92-1.87 (m, 2H), 1.70-1.67 (m, 4H), 1.48 (s, 6H)

Workup

customThe resultant mixture was purified by reverse phase combiflash
washeluting with 0-50% gradient of CH3CN in 0.5% NH4HCO3

Sources & evidence

ORD record: ord-cf98d58415524cc8895527fe7f128300
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090628B2

Reaction notes

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