4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole → N-((2-(1H-indazol-4-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)-N-methylsulfonyl-1-methylpyrrolidin-3-amine

HRID 2098706Notes

Reaction equation

HRID 2098706 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:5]2[S:10][C:9]([CH2:11][N:12]([CH:17]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18]3)[S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:37]2[CH:45]=[CH:44][CH:43]=[C:42]3[C:38]=2[CH:39]=[N:40][NH:41]3)O1>>[NH:41]1[C:42]2[C:38](=[C:37]([C:2]3[N:3]=[C:4]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[C:5]4[S:10][C:9]([CH2:11][N:12]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:17]5[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18]5)=[CH:8][C:6]=4[N:7]=3)[CH:45]=[CH:44][CH:43]=2)[CH:39]=[N:40]1

Participants

3

Reactant 2

HCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 86618408N-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-N-(1-methyl-pyrrolidin-3-yl)-methanesulfonamide

Product 1

HCID 59593139N-((2-(1H-indazol-4-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)-N-methylsulfonyl-1-methylpyrrolidin-3-amine

Procedure

N-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-N-(1-methyl-pyrrolidin-3-yl)-methanesulfonamide was reacted with 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indazole in General Procedure A to yield 195. NMR: (CDCl3): 1.96 (1H,m); 2.19 (2H,m); 2.33 (4H,m); 2.48 (1H,m); 2.90 (5H,m); 3.94 (4H,m); 4.10 (4H,m); 4.57 (1H,m); 4.90 (2H,s); 7.50 (1H,s); 7.53 (1H,d,J=7.4Hz); 7.10 (1H,d,J=8.2Hz); 8.30 (1H,d,J=7.1Hz); 9.03 (1H,s); 10.14 (1H, br s). MS: (ESI+): MH+=528

Sources & evidence

ORD record
ord-9746ad8908e3435591e9294114bfbdc5
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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