2,6-Lutidine → HCID 59593007, compound

HRID 2262257Notes

Reaction equation

HRID 2262257 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH2:11][NH2:12])=[CH:8][C:6]=2[N:7]=1.N1C(C)=CC=CC=1C.[CH:27]1([NH:30][C:31](=[O:34])[CH2:32]Cl)[CH2:29][CH2:28]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>CN(C=O)C>[NH:47]1[C:48]2[C:44](=[C:43]([C:2]3[N:3]=[C:4]([N:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)[C:5]4[S:10][C:9]([CH2:11][NH:12][CH2:32][C:31]([NH:30][CH:27]5[CH2:29][CH2:28]5)=[O:34])=[CH:8][C:6]=4[N:7]=3)[CH:51]=[CH:50][CH:49]=2)[CH:45]=[N:46]1

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 7357802-chloro-N-cyclopropylacetamideHCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 46180727(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanamine

Product 1

HCID 59593007HCID 59593007, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanamine 27 from Example 11 (110 mg, 0.39 mM) in 5 mL DMF was added 48.2 uL (1.06 eq) 2,6-lutidine and N1-cyclopropyl-2-chloroacetamide (1.2 eq) followed by Suzuki coupling of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)1H-indazole 7 as per General Procedure K. Complete reaction was confirmed by LCMS and the reaction was concentrated in vacuo to give 6.5 mg of 382 after RP-HPLC purification (40% yield). MS (Q1) 464.3 (M)+

Workup

  1. customComplete reaction
  2. concentrationthe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-f51e764cd090410697367705bd3f94d4
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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