2-Acetyl-3-bromo-benzothiophene → 1-(3-(6-((4-(Dimethylamino)piperidin-1-yl)methyl)-4-morpholinothieno[3,2-d]pyrimidin-2-yl)benzo[b]thiophen-2-yl)ethanone

HRID 1945786Notes

Reaction equation

HRID 1945786 reaction equation
[CH3:1][N:2]([CH3:38])[CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[S:18][C:17]3[C:16]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[N:15][C:14]([Sn](CCCC)(CCCC)CCCC)=[N:13][C:12]=3[CH:11]=2)[CH2:5][CH2:4]1.Br[C:40]1[C:41]2[CH:51]=[CH:50][CH:49]=[CH:48][C:42]=2[S:43][C:44]=1[C:45](=[O:47])[CH3:46]>>[CH3:1][N:2]([CH3:38])[CH:3]1[CH2:4][CH2:5][N:6]([CH2:9][C:10]2[S:18][C:17]3[C:16]([N:19]4[CH2:20][CH2:21][O:22][CH2:23][CH2:24]4)=[N:15][C:14]([C:40]4[C:41]5[CH:51]=[CH:50][CH:49]=[CH:48][C:42]=5[S:43][C:44]=4[C:45](=[O:47])[CH3:46])=[N:13][C:12]=3[CH:11]=2)[CH2:7][CH2:8]1

Participants

3

Reactant 2

HCID 107061652-Acetyl-3-bromo-benzothiopheneHCID 59605498Dimethyl-[1-(4-morpholin-4-yl-2-(tributylstannanyl)thieno[3,2-d]pyrimidin-6-ylmethyl)piperidin-4-yl]amine

Product 1

HCID 498322731-(3-(6-((4-(Dimethylamino)piperidin-1-yl)methyl)-4-morpholinothieno[3,2-d]pyrimidin-2-yl)benzo[b]thiophen-2-yl)ethanone

Procedure

Following General Procedure G for Stille coupling, N,N-dimethyl-1-((4-morpholino-2-(tributylstannyl)thieno[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-amine and 1-(3-bromobenzo[b]thiophen-2-yl)ethanone were reacted to give 208. LCMS m/z: 536.7 (MH+)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-aeed43af0850470f952cf30a9807e18f
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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