Triethylamine → HCID 68866379, compound

HRID 1725966Notes

Reaction equation

[Cl:1][C:2]1[C:10]([CH2:11][CH3:12])=[CH:9][CH:8]=[C:7]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2F)(=[O:16])=[O:15])[C:3]=1[C:4]([OH:6])=[O:5].[CH3:24][N:25]([CH2:27][CH2:28][CH2:29][CH2:30][NH2:31])[CH3:26].C(N(CC)CC)C>C(#N)C>[Cl:1][C:2]1[C:10]([CH2:11][CH3:12])=[CH:9][CH:8]=[C:7]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[NH:31][CH2:30][CH2:29][CH2:28][CH2:27][N:25]([CH3:26])[CH3:24])(=[O:16])=[O:15])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of Example 389B (133 mg, 0.4 mmol), 4-(N,N-dimethylamino)butylamine (346 mg, 3.0 mmol), acetonitrile (3 mL), and triethylamine (0.3 mL, 1.9 mmol) was sealed in a vial and shaken at to 80° C. for 72 hours. The mixture was purified by preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile/10 mmol aqueous ammonium acetate over 8 minutes (10 minute run time) at a flow rate of 40 mL/min to provide the desired product. MS (ESI(+)) m/e 454 (M+H)+; (ESI(−)) m/e 452 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 7.64 (d, 1H), 7.43 (d, 1H), 7.36 (m, 1H), 7.16 (d, 1H), 6.77 (d, 1H), 6.61 (t, 1H), 5.78 (br s, 1H), 3.31 (br s, 2H), 3.23 (m, 2H), 3.04 (m, 2H), 2.76 (s, 6H), 2.59 (q, 2H), 1.86 (m, 2H), 1.66 (m, 2H), 1.09 (t, 3H).

Workup

customThe mixture was purified by preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size)
customover 8 minutes
custom(10 minute run time)

Sources & evidence

ORD record: ord-fa22d3e37375456c820b188fd8b439c1
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491718B2

Reaction notes

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