4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole → HCID 131728569, compound

HRID 2262061Notes

Reaction equation

[C:1]([O:5][C:6](=[O:36])[NH:7][CH:8]([CH2:10][C:11](=[O:35])[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[S:27][C:26]3[C:25]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[N:24][C:23](Cl)=[N:22][C:21]=3[CH:20]=2)[CH:14]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].CC1(C)C(C)(C)OB([C:45]2[CH:53]=[CH:52][CH:51]=[C:50]3[C:46]=2[CH:47]=[N:48][NH:49]3)O1>>[C:1]([O:5][C:6](=[O:36])[NH:7][CH:8]([CH2:10][C:11](=[O:35])[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[S:27][C:26]3[C:25]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[N:24][C:23]([C:45]4[CH:53]=[CH:52][CH:51]=[C:50]5[C:46]=4[CH:47]=[N:48][NH:49]5)=[N:22][C:21]=3[CH:20]=2)[CH:14]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

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

HCID 131728570HCID 131728570, compound

Product 1

HCID 131728569HCID 131728569, compound

Procedure

3-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)benzenamine (50 mg) was reacted with Boc-2-aminoisobutric acid via General Procedure I to give tert-butyl(3-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)phenylcarbamoyl)propan-2-ylcarbamate. 75 mg of the crude tert-butyl(3-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)phenylcarbamoyl)propan-2-ylcarbamate 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)propan-2-ylcarbamate.

Sources & evidence

ORD record: ord-77f164cfdc314b8ba07447a63596e886
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846929B2

Reaction notes

Loading…