Cyclopropanesulfonyl chloride → HCID 59592849, compound

HRID 2098824Notes

Reaction equation

HRID 2098824 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.[CH:19]1([S:22](Cl)(=[O:24])=[O:23])[CH2:21][CH2:20]1.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:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)[C:5]4[S:10][C:9]([CH2:11][NH:12][S:22]([CH:19]5[CH2:21][CH2:20]5)(=[O:24])=[O:23])=[CH:8][C:6]=4[N:7]=3)[CH:42]=[CH:41][CH:40]=2)[CH:36]=[N:37]1

Participants

4

Reactant 3

HCID 2760919Cyclopropanesulfonyl chlorideHCID 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 59592849HCID 59592849, compoundYield 40%

Procedure

(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanamine 27 from Example 11 (53.2 mg, 0.19 mM) was reacted with cyclopropane sulfonylchloride (2.2 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 16.7 mg of 376 after RP-HPLC purification (40% yield). MS (Q1) 471.3 (M)+

Workup

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

Sources & evidence

ORD record
ord-2c6b5f95d0f448df89760f505943b6a3
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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