1-Methylpyrrolidine → 1-{6-[(2-{[7-(2,4-Dichlorophenyl)imidazo[1,2-c]pyrimidin-5-yl]amino}ethyl)amino]pyridin-3-yl}ethanone

HRID 2171557Notes

Reaction equation

HRID 2171557 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16]1[N:21]=[C:20]([NH:22][CH2:23][CH2:24][NH2:25])[N:19]2[CH:26]=[CH:27][N:28]=[C:18]2[CH:17]=1.CN1CCCC1.Cl[C:36]1[N:41]=[CH:40][C:39]([C:42](=[O:44])[CH3:43])=[CH:38][CH:37]=1.CCN(C(C)C)C(C)C>>[Cl:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16]1[N:21]=[C:20]([NH:22][CH2:23][CH2:24][NH:25][C:36]2[N:41]=[CH:40][C:39]([C:42](=[O:44])[CH3:43])=[CH:38][CH:37]=2)[N:19]2[CH:26]=[CH:27][N:28]=[C:18]2[CH:17]=1

Participants

5

Reactant 4

HCID 84541-MethylpyrrolidineHCID 81531DiisopropylethylamineHCID 27796981-(6-Chloropyridin-3-yl)ethan-1-oneHCID 68710578N-[7-(2,4-Dichlorophenyl)imidazo[1,2-c]pyrimidin-5-yl]ethane-1,2-diamine trifluoroacetate

Product 1

HCID 593130281-{6-[(2-{[7-(2,4-Dichlorophenyl)imidazo[1,2-c]pyrimidin-5-yl]amino}ethyl)amino]pyridin-3-yl}ethanone

Conditions

Temperature
130 °C

Procedure

50 mg (0.155 mmol) of the amine (Example 8A) are introduced into 3 ml of dry N-methylpyrrolidine, 48.3 mg (0.31 mmol) of 1-(6-chloropyridin-3-yl)ethanone and 40.1 mg (0.31 mmol) of DIPEA are added, and the mixture is heated in a microwave at 130° C. for 1.5 h. Purification by preparative HPLC results in 11 mg (15% of theory) of the product as a solid.

Workup

  1. additionare added
  2. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-a12be82d802c42b1a56d0b9827a240fc
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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