4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole → HCID 131728571, compound

HRID 2098643Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[C:5]2[S:10][C:9]([C:11]3[CH:12]=[C:13]([NH:17][C:18]([CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:19])[CH:14]=[CH:15][CH:16]=3)=[CH:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:43]2[CH:51]=[CH:50][CH:49]=[C:48]3[C:44]=2[CH:45]=[N:46][NH:47]3)O1>>[C:24]([O:23][C:22](=[O:28])[NH:21][CH2:20][C:18](=[O:19])[NH:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:9]2[S:10][C:5]3[C:4]([N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[N:3][C:2]([C:43]4[CH:51]=[CH:50][CH:49]=[C:48]5[C:44]=4[CH:45]=[N:46][NH:47]5)=[N:7][C:6]=3[CH:8]=2)[CH:12]=1)([CH3:27])([CH3:26])[CH3:25]

Participants

Reactant 2

HCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole

HCID 86624222HCID 86624222, compound

Product 1

HCID 131728571HCID 131728571, compound

Procedure

3-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)benzenamine (50 mg) was reacted with Boc-glycine via General Procedure I to give tert-butyl(3-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)phenylcarbamoyl)methylcarbamate. 70 mg of the crude tert-butyl (3-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)phenylcarbamoyl)methylcarbamate was coupled to 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 7 via General Procedure A to yield tert-butyl(3-(2-(1H-indazol-4-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)phenylcarbamoyl)methylcarbamate.

Sources & evidence

ORD record: ord-f9a26d072c944d869221a418493808c3
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450315B2

Reaction notes

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