3-Methoxyphenylacetyl chloride → HCID 59592922, compound

HRID 2262253Notes

Reaction equation

HRID 2262253 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.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH2:27][C:28](Cl)=[O:29])[CH:24]=[CH:25][CH:26]=1.CC1(C)C(C)(C)OB([C:39]2[CH:47]=[CH:46][CH:45]=[C:44]3[C:40]=2[CH:41]=[N:42][NH:43]3)O1>>[NH:43]1[C:44]2[C:40](=[C:39]([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][C:28](=[O:29])[CH2:27][C:23]5[CH:24]=[CH:25][CH:26]=[C:21]([O:20][CH3:19])[CH:22]=5)=[CH:8][C:6]=4[N:7]=3)[CH:47]=[CH:46][CH:45]=2)[CH:41]=[N:42]1

Participants

4

Reactant 3

HCID 27332463-Methoxyphenylacetyl 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 59592922HCID 59592922, compoundYield 33%

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 3-methoxyphenylacetyl chloride (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 16.0 mg of 377 after RP-HPLC purification (33% yield). MS (Q1) 515.3 (M)+

Workup

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

Sources & evidence

ORD record
ord-1149d9e8f5714b128882b1a258373ade
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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