Cesium carbonate → HCID 118433803, compound

HRID 1052514Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[C:3]=1Br.[CH2:29]([NH:31][C:32]1[N:37]=[CH:36][C:35](B(O)O)=[CH:34][C:33]=1[NH:41][S:42]([C:45]1[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=1)(=[O:44])=[O:43])[CH3:30].C(=O)([O-])[O-].[Cs+].[Cs+]>>[NH2:1][C:2]1[C:3]([C:35]2[CH:34]=[C:33]([NH:41][S:42]([C:45]3[CH:46]=[CH:47][C:48]([O:51][CH3:52])=[CH:49][CH:50]=3)(=[O:44])=[O:43])[C:32]([NH:31][CH2:29][CH3:30])=[N:37][CH:36]=2)=[C:4]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[N:5]=[CH:6][N:7]=1

Participants

Reactant 3

HCID 10796Cesium carbonate

HCID 90102168HCID 90102168, compound

HCID 118433733HCID 118433733, compound

Product 1

HCID 118433803HCID 118433803, compoundYield 48%

Procedure

(S)-2-(1-((6-Amino-5-bromopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (25 mg, 0.06 mmol) was treated with 6-(ethylamino)-5-(4-methoxyphenylsulfonamido)pyridin-3-ylboronic acid (30 mg, 0.09 mmol), 2M cesium carbonate (60 μl, 0.12 mmol) and bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (3 mg, 0.01 mmol) according to the method described in Example 3 to give 18 mg (48% yield) of the title compound as a solid. Purity 100%.

Sources & evidence

ORD record: ord-65aee502229d47c58a1f0ef32df0c1af
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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