Sodium Hydroxide → Ethyl hydrogen 4-(2-amino-5-(thiophen-2-yl)phenylcarbamoyl)phenylphosphonate

HRID 1013449Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:4][C:3]=1[NH:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([P:22](=[O:29])([O:26]CC)[O:23][CH2:24][CH3:25])=[CH:18][CH:17]=1)=[O:15].[OH-].[Na+]>O1CCOCC1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:4][C:3]=1[NH:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([P:22](=[O:26])([OH:29])[O:23][CH2:24][CH3:25])=[CH:18][CH:17]=1)=[O:15]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of diethyl [4-({[2-amino-5-(2-thienyl)phenyl]amino}carbonyl)phenyl]phosphonate (24.2 mg, 0.0562 mmol) (24.2 mg, 0.0562 mmol), dioxane (140 uL) and 5N aqueous NaOH (140 uL) was heated to 80° C. (oil bath temperature) for 1 h. The reaction was quenched with TFA (˜140 uL) and concentrated. The residue was purified by HPLC (25-80% MeCN in H2O with 0.025% TFA) to afford the requisite product. 1H NMR (DMSO-d6, 600 MHz) δ 9.77 (s, 1H), 8.30 (t, J=8.3 Hz, 2H), 7.69-7.64 (m, 2H), 7.48-7.45 (m, 1H), 7.34-7.31 (m, 1H), 7.26 (dd, J=8.2, 2.0 Hz, 1H), 7.22 (d, J=2.6 Hz, 1H), 7.02 (dd, J=5.0, 3.5 Hz, 1H), 6.79 (d, J=8.5 Hz, 1H), 5.16 (s, 2H), 3.6-3.54 (m, 2H), 1.05 (t, J=7.04 Hz, 3H). MS: cal'd 403 (MH+), exp 403 (MH+).

Workup

customThe reaction was quenched with TFA (˜140 uL)
concentrationconcentrated
customThe residue was purified by HPLC (25-80% MeCN in H2O with 0.025% TFA)
customto afford the requisite product

Sources & evidence

ORD record: ord-51b36083823942c7b7aa65e77600412b
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981874B2

Reaction notes

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