Acetyl chloride → HCID 59592939, compound

HRID 2098849Notes

Reaction equation

HRID 2098849 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.[C:20](Cl)(=[O:22])[CH3:21].[NH:24]1[C:32]2[C:27](=[CH:28][C:29](B(O)O)=[CH:30][CH:31]=2)[CH:26]=[CH:25]1>>[NH:24]1[C:32]2[C:27](=[CH:28][C:29]([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:20](=[O:22])[CH3:21])=[CH:8][C:6]=4[N:7]=3)=[CH:30][CH:31]=2)[CH:26]=[CH:25]1

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 27343615-Indolylboronic acidHCID 595929371-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-methylmethanamine

Product 1

HCID 59592939HCID 59592939, compoundYield 44%

Procedure

1-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-methylmethanamine 55 from Example 11a was reacted with acetyl chloride (1.2 eq) followed by Suzuki coupling of indole-5-boronic acid as per General Procedure K. Complete reaction was confirmed by LCMS and the reaction was concentrated in vacuo to give 33.1 mg of 392 after RP-HPLC purification (44% yield). MS (Q1) 422.2 (M)+

Workup

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

Sources & evidence

ORD record
ord-778189ce70144514806979e5cfd4ea93
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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