6-(4-Ethylpiperazin-1-yl)pyridin-3-amine → N-(3-(4-amino-2-(6-(4-ethylpiperazin-1-yl)pyridin-3-ylamino)thieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamide

HRID 1485499Notes

Reaction equation

HRID 1485499 reaction equation
[NH2:1][C:2]1[C:3]2[S:11][CH:10]=[C:9]([C:12]3[CH:13]=[C:14]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH:15]=[CH:16][CH:17]=3)[C:4]=2[N:5]=[C:6](Cl)[N:7]=1.[CH2:23]([N:25]1[CH2:30][CH2:29][N:28]([C:31]2[N:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=2)[CH2:27][CH2:26]1)[CH3:24]>>[NH2:1][C:2]1[C:3]2[S:11][CH:10]=[C:9]([C:12]3[CH:13]=[C:14]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH:15]=[CH:16][CH:17]=3)[C:4]=2[N:5]=[C:6]([NH:37][C:34]2[CH:35]=[N:36][C:31]([N:28]3[CH2:29][CH2:30][N:25]([CH2:23][CH3:24])[CH2:26][CH2:27]3)=[CH:32][CH:33]=2)[N:7]=1

Participants

3

Reactant 2

HCID 91616746-(4-Ethylpiperazin-1-yl)pyridin-3-amineHCID 86675656N-(3-(4-amino-2-chlorothieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamide

Product 1

HCID 53238657N-(3-(4-amino-2-(6-(4-ethylpiperazin-1-yl)pyridin-3-ylamino)thieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamideYield 74.9%

Procedure

The target compound of Example 27 (22 mg, 74% yield) was prepared in the same manner as Step 9 of Example 1 using N-(3-(4-amino-2-chlorothieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamide (20 mg, 0.056 mmol) and 6-(4-ethylpiperazin-1-yl)pyridin-3-amine (31 mg, 0.17 mmol).

Sources & evidence

ORD record
ord-95e9135a48264c79843d8c0d9b1a0d07
Source dataset
uspto-grants-2016_08
Patent number
US09422307B2

Reaction notes

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