Triethylamine → HCID 58529328, compound

HRID 1972779Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[C:17]([CH2:25][CH2:26][CH2:27][CH2:28]Br)[N:18]3[C:23]=2[C:22]([NH2:24])=[N:21][CH:20]=[N:19]3)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1.C(N(CC)CC)C>CN(C=O)C.[I-].[Na+]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[C:17]([CH2:25][CH2:26][CH2:27][CH2:28][N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[N:18]3[C:23]=2[C:22]([NH2:24])=[N:21][CH:20]=[N:19]3)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 5-[3-(benzyloxy)phenyl]-7-(4-bromobutyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (129 mg, 0.29 mmol) in DMF (1.5 mL) was added pyrrolidine (26 μL, 0.31 mmol), triethylamine (120 μl, 0.86 mmol), and sodium iodide (0.4 mg, 0.003 mmol). The reaction was heated (55° C.) for 17 h and then cooled to rt. The mixture was partitioned between ethyl acetate (25 mL) and water (25 mL). The layers were separated and the organic was washed with water (2×20 mL), brine, dried (Na2SO4) and evaporated to afford 121 mg (96%) of the desired product. 1H NMR (300 MHz, DMSO-d6) δ7.87 (s, 1 H), 7.46-7.41 (m, 2 H), 7.41-7.28 (m, 4 H), 7.08-7.04 (m, 1 H), 7.02-6.97 (m, 2 H), 6.55 (s, 1 H), 5.14 (s, 2H), 2.87 (t, 2 H), 2.42-2.33 (m, 6 H), 1.76-1.66 (m, 2 H), 1.67-1.60 (m, 4 H), 1.56-1.46 (m, 2 H); ES-MS m/z 442.2 [M+H]+, HPLC RT (min) 2.30.

Workup

temperaturecooled to rt
customThe mixture was partitioned between ethyl acetate (25 mL) and water (25 mL)
customThe layers were separated
washthe organic was washed with water (2×20 mL), brine
dry with materialdried (Na2SO4)
customevaporated

Sources & evidence

ORD record: ord-1d494c83730346618e493acaf926adbd
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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