5-(1H-indol-2-yl)-2-methoxy-phenylamine → (4-{3-[5-(1h-Indol-2-yl)-2-methoxy-phenyl]-thioureido}-benzyl)-phosphonic acid diethyl ester

HRID 25513

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([O:17][CH3:18])=[C:14]([NH2:16])[CH:15]=1.[N:19]([C:22]1[CH:36]=[CH:35][C:25]([CH2:26][P:27](=[O:34])([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])=[CH:24][CH:23]=1)=[C:20]=[S:21]>O1CCCC1>[CH2:29]([O:28][P:27]([CH2:26][C:25]1[CH:24]=[CH:23][C:22]([NH:19][C:20]([NH:16][C:14]2[CH:15]=[C:10]([C:2]3[NH:1][C:9]4[C:4]([CH:3]=3)=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH:11]=[CH:12][C:13]=2[O:17][CH3:18])=[S:21])=[CH:36][CH:35]=1)(=[O:34])[O:31][CH2:32][CH3:33])[CH3:30]

Participants

Conditions

Temperature: 50 °C

Procedure

The product from Example 1 (0.119 g, 0.5 mmol) and the product from Example 23, Step A (0.157 g, 0.54 mmol) were combined in tetrahydrofuran (8 mL), briefly heated to 50° C., and then allowed to stand for 6 hours at room temperature. The reaction mixture was concentrated to dryness and the residue triturated with hexanes/ethyl acetate. The product was collected by filtration (0.14 g), mp softening at 120° C., gradual decomposition.

Workup

concentrationThe reaction mixture was concentrated to dryness
customthe residue triturated with hexanes/ethyl acetate
filtrationThe product was collected by filtration (0.14 g), mp softening at 120° C.

Sources & evidence

ORD record: ord-b6636ae04dcd49b496eab737963808b0
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06858739B2

Linked notes

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