Methoxyacetyl chloride → HCID 59592952, compound

HRID 2262284Notes

Reaction equation

HRID 2262284 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[S:10][C:9]([CH2:11][NH:12][CH3:13])=[CH:8][C:6]=2[N:7]=1.[CH3:20][O:21][CH2:22][C:23](Cl)=[O:24].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:14]4[CH2:19][CH2:18][O:17][CH2:16][CH2:15]4)[C:5]4[S:10][C:9]([CH2:11][N:12]([CH3:13])[C:23](=[O:24])[CH2:22][O:21][CH3:20])=[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 96623Methoxyacetyl 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 59592952HCID 59592952, compoundYield 52%

Procedure

1-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-methylmethanamine 55 from Example 1a (0.22 g) was reacted with methoxyacetyl 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. Complete reaction was confirmed by LCMS and the reaction was concentrated in vacuo to give 52.7 mg of 403 after RP-HPLC purification (52% yield). MS (Q1) 453.2 (M)+

Workup

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

Sources & evidence

ORD record
ord-dcdbe36e23924632abad74f6789a7adf
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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