Lithium Hydroxide → HCID 59592887, compound

HRID 2262289Notes

Reaction equation

HRID 2262289 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:14]2CCOCC2)[C:5]2[S:10][C:9]([CH2:11][NH:12][CH3:13])=[CH:8][C:6]=2[N:7]=1.C([O:23][CH2:24][C:25](Cl)=[O:26])(=O)C.CC1(C)C(C)(C)OB([C:36]2[CH:44]=[CH:43][CH:42]=[C:41]3[C:37]=2[CH:38]=[N:39][NH:40]3)O1.[Li+].[OH-].[CH2:48]1[CH2:52][O:51][CH2:50][CH2:49]1>CO>[NH:40]1[C:41]2[C:37](=[C:36]([C:2]3[N:3]=[C:4]([N:14]4[CH2:48][CH2:52][O:51][CH2:50][CH2:49]4)[C:5]4[S:10][C:9]([CH2:11][N:12]([CH3:13])[C:24](=[O:23])[CH2:25][OH:26])=[CH:8][C:6]=4[N:7]=3)[CH:44]=[CH:43][CH:42]=2)[CH:38]=[N:39]1

Participants

7

Reactant 5

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 26297Acetoxyacetyl chlorideHCID 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 59592887HCID 59592887, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-methylmethanamine 55 from Example 11a (0.22 g) was reacted with acetoxyacetyl chloride (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. The resulting compound was dissolved in 2 mL THF and 2 mL MeOH followed by the addition of 2 mL 1M LiOH and the resulting solution stirred for 2.5 hours. Complete reaction was confirmed by LCMS and the reaction was concentrated in vacuo to give 31.1 mg of 409 after RP-HPLC purification (24% yield). MS (Q1) 439.2 (M)+.

Workup

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

Sources & evidence

ORD record
ord-a013b760765f4139893fc9d56bb18f8a
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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