4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole → HCID 59592840, compound

HRID 2262274Notes

Reaction equation

HRID 2262274 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[S:10][C:9]([CH2:11][NH:12][CH3:13])=[CH:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:28]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:29]=2[CH:30]=[N:31][NH:32]3)O1>>[NH:32]1[C:33]2[C:29](=[C:28]([C:2]3[N:3]=[C:4]([N:14]4[CH2:19][CH2:18][O:17][CH2:16][CH2:15]4)[C:5]4[S:10][C:9]([CH2:11][NH:12][CH3:13])=[CH:8][C:6]=4[N:7]=3)[CH:36]=[CH:35][CH:34]=2)[CH:30]=[N:31]1

Participants

3

Reactant 2

HCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 595929371-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-methylmethanamine

Product 1

HCID 59592840HCID 59592840, compoundYield 28%

Procedure

1-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-methylmethanamine 55 from Example 11a was reacted with 0.18 g (1.3 eq) of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)1H-indazole 7 as per General Procedure A to give 18 mg of 389 after RP-HPLC purification (28% yield). MS (Q1) 381.2 (M)+

Sources & evidence

ORD record
ord-bc66dc1b81c6425b97ddfe890db9b2ce
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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