Methanesulfonyl chloride → HCID 59593165, compound

HRID 2262276Notes

Reaction equation

HRID 2262276 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[S:10][C:9]([CH2:11][NH:12][CH3:13])=[C:8]([CH3:14])[C:6]=2[N:7]=1.[CH3:21][S:22](Cl)(=[O:24])=[O:23].CC1(C)C(C)(C)OB([C:34]2[CH:42]=[CH:41][CH:40]=[C:39]3[C:35]=2[CH:36]=[N:37][NH:38]3)O1>>[NH:38]1[C:39]2[C:35](=[C:34]([C:2]3[N:3]=[C:4]([N:15]4[CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)[C:5]4[S:10][C:9]([CH2:11][N:12]([S:22]([CH3:21])(=[O:24])=[O:23])[CH3:13])=[C:8]([CH3:14])[C:6]=4[N:7]=3)[CH:42]=[CH:41][CH:40]=2)[CH:36]=[N:37]1

Participants

4

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 59817854(2-chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-methylmethanamine

Product 1

HCID 59593165HCID 59593165, compoundYield 29%

Procedure

1-(2-Chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-methylmethanamine 56 from Example 11b was reacted with methanesulfonylchloride (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 31.0 mg of 391 after RP-HPLC purification (29% yield). MS (Q1) 473.2 (M)+

Workup

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

Sources & evidence

ORD record
ord-80f2a8b2e3724efba3533c749b91b6ff
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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