Triethylamine → HCID 68524673, compound

HRID 1437424Notes

Reaction equation

[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:18]([F:19])=[CH:17][C:13](C(O)=O)=[C:12]([NH:20][C@H:21]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)[CH3:22])[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.C([N:32]([CH2:35]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:44])=CC=1>CC(O)(C)C>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[N:11]=[C:12]4[N:20]([C@H:21]([C:23]5[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=5)[CH3:22])[C:35](=[O:44])[NH:32][C:13]4=[CH:17][C:18]=3[F:19])[CH:5]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 83 °C

Procedure

A mixture of (S)-6-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-2-(1-(4-fluorophenyl)ethylamino)nicotinic acid (Method 40; 0.03 g, 0.08 mmol), triethylamine (0.02 g, 0.22 mmol), and DPPA (0.04 g, 0.15 mmol) in t-BuOH (2 ml) was heated to 83° C. for 5 hours. The reaction was cooled, concentrated, and then dissolved in DCM (30 ml). The organic layer was washed with water (50×2 ml), dried, filtered, and concentrated. The resulting solid was purified by column chromatography (DCM:MeOH=15:1) to give the title compounds (0.01 g, 30%). NMR (400 MHz, CD3OD) 7.48-7.44 (m, 2H), 7.24 (d, J=10.3 Hz, 1H), 7.06-7.02 (m, 2H), 5.93 (br s, 1H), 5.76-5.71 (m, 1H), 1.99 (d, J=7.2 Hz, 3H), 1.90-1.84 (m, 1H), 0.96-0.94 (m, 2H), 0.64-0.63 (m, 2H). MS: Calcd.: 396. Found: [M+H]+ 397.

Workup

temperatureThe reaction was cooled
concentrationconcentrated
dissolutiondissolved in DCM (30 ml)
washThe organic layer was washed with water (50×2 ml)
customdried
filtrationfiltered
concentrationconcentrated
customThe resulting solid was purified by column chromatography (DCM:MeOH=15:1)

Sources & evidence

ORD record: ord-c56cd3a94ca346ff979da0bceec90de8
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622482B2

Reaction notes

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