Triethylamine → HCID 68866410, compound

HRID 1725953Notes

Reaction equation

[Br:1][C:2]1[C:3]([O:22][CH3:23])=[C:4]([C:8]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2F)(=[O:14])=[O:13])=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].C(N(CC)CC)C.[CH3:31][N:32]([CH3:39])[CH2:33][C:34]([CH3:38])([CH3:37])[CH2:35][NH2:36]>C(#N)C>[Br:1][C:2]1[C:3]([O:22][CH3:23])=[C:4]([C:8]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[NH:36][CH2:35][C:34]([CH3:38])([CH3:37])[CH2:33][N:32]([CH3:39])[CH3:31])(=[O:14])=[O:13])=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of Example 371A (150 mg, 0.37 mmol), acetonitrile (2.5 mL), triethylamine (0.26 mL, 1.86 mmol), and N,N,2,2-tetramethyl-1,3-propanediamine (381 mg, 3.0 mmol) was sealed in a vial and shaken at 65° C. for 144 hours and heated to 80° C. for 18 hours. The mixture was concentrated and the residue 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 514, 516 (M+H)+; (ESI(−)) m/e 512, 514 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 12.07 (br s, 1H), 7.61 (d, 1H), 7.38 (d, 1H), 7.31 (t, 1H), 7.01 (d, 1H), 6.85 (t, 1H), 6.63 (t, 1H), 5.75 (s, 1H), 3.68 (s, 3H), 3.26 (br s, 1H), 3.09 (m, 4H), 2.79 (br s, 6H), 1.07 (s, 6H).

Workup

temperatureheated to 80° C. for 18 hours
concentrationThe mixture was concentrated
customthe residue was purified by preparative HPLC on a
customover 8 minutes
custom(10 minute run time)

Sources & evidence

ORD record: ord-7f5a36311c104018aef4b694beba03b2
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491718B2

Reaction notes

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