Triethylamine → HCID 16075331, compound

HRID 1795126Notes

Reaction equation

[F:1][C:2]([F:33])([F:32])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH:19][C:20](OC2C=CC([N+]([O-])=O)=CC=2)=[O:21])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[NH2:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1.CCN(CC)CC>C1COCC1>[F:32][C:2]([F:1])([F:33])[C:3]1[CH:4]=[CH:5][C:6]([S:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH:19][C:20]([NH:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)=[O:21])(=[O:10])=[O:11])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

2-{[(4-nitrophenoxy)carbonyl]amino}phenyl 4-(trifluoromethyl)-benzenesulfonate (0.25 mmol, 120 mg) is dissolved in THF, and 2-(aminomethyl)pyridine (0.25 mmol, 26 μl) and Et3N (0.3 mmol, 42 μl) are added to the solution. The reaction mixture is heated at 60° C. for overnight. After purification by preparative HPLC, 2-({[(pyridin-2-ylmethyl)amino]carbonyl}amino)phenyl 4-(trifluoromethyl)benzenesulfonate is obtained in 45% yield. 1H NMR (400 MHz, MeOD-d6) 8.54 (d, 1H), 8.01(d, 2H), 7.82(m, 4H), 7.42(d, 1H), 7.34(t, 1H), 7.26(m, 4H), 7.05(t, 1H), 4.41(s, 2H). ESI+ for C20H16F3N3O4S m/z=452, (M+H)+.

Workup

customAfter purification by preparative HPLC

Sources & evidence

ORD record: ord-41575ec835204633b5f38cbb9ad23037
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07026339B2

Reaction notes

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