Thiosemicarbazide → (S)-2-(1-((5-(5-Amino-1,3,4-thiadiazol-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052770Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9](=[O:11])[N:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:7]([C@@H:18]([NH:20][C:21]1[C:22]3[C:29]([C:30](O)=O)=[CH:28][NH:27][C:23]=3[N:24]=[CH:25][N:26]=1)[CH3:19])=[N:6]2.[NH:33]([C:35](=[S:37])[NH2:36])[NH2:34].O(Cl)Cl.[P+5]>O1CCOCC1>[NH2:36][C:35]1[S:37][C:30]([C:29]2[C:22]3[C:21]([NH:20][C@H:18]([C:7]4[N:8]([C:12]5[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=5)[C:9](=[O:11])[C:10]5=[C:2]([CH3:1])[CH:3]=[CH:4][N:5]5[N:6]=4)[CH3:19])=[N:26][CH:25]=[N:24][C:23]=3[NH:27][CH:28]=2)=[N:34][N:33]=1

Participants

Conditions

Temperature: 110 °C

Procedure

(S)-4-((1-(5-Methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid (50 mg, 0.12 mmol) was treated with hydrazinecarbothioamide (20 mg, 0.22 mmol) and phosphorus (V) oxychloride (12.5 μl, 0.13 mmol) in 1,4-dioxane (1 ml) according to the method described in Example 120 but stirring at 110° C. overnight. The residue was purified using SP1® Purification System (reverse phase, 0% to 100%, water-methanol/acetonitrile 1:1) to give 11 mg (19% yield) of the title compound.

Workup

customThe residue was purified
customSP1® Purification System (reverse phase, 0% to 100%, water-methanol/acetonitrile 1:1)

Sources & evidence

ORD record: ord-04fe65b509284d3bab70ce775b329c6c
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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