Methanol → [4-(6-Aminomethyl-benzo[b]thiophen-2-yl)-pyrimidin-2-yl]-[3-(4-methyl-piperazin-1-yl)-propyl]-amine

HRID 1986193Notes

Reaction equation

HRID 1986193 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH2:24][CH2:25][CH2:26][N:27]4[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]4)[N:18]=3)[S:14][C:13]=2[CH:34]=1)(C)(C)C.C(O)(C(F)(F)F)=O.CO>ClCCl>[NH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH2:24][CH2:25][CH2:26][N:27]4[CH2:28][CH2:29][N:30]([CH3:33])[CH2:31][CH2:32]4)[N:18]=3)[S:14][C:13]=2[CH:34]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 68859103(2-{2-[3-(4-Methylpiperazin-1-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophen-6-ylmethyl)-carbamic acid tert-butyl ester

Product 1

HCID 68902579[4-(6-Aminomethyl-benzo[b]thiophen-2-yl)-pyrimidin-2-yl]-[3-(4-methyl-piperazin-1-yl)-propyl]-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-{2-[3-(4-Methylpiperazin-1-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophen-6-ylmethyl)-carbamic acid tert-butyl ester (1.36 g, 2.74 mmol) is dissolved in dichloromethane (20 mL) and TFA (3.2 mL) is added. After stirring for 20 hours, methanol is added and the mixture is passed through an SCX column. After eluting with methanol to remove the salts, 20% 2.0 M NH3/MeOH)/EtOAC is used to elute the product which is then passed through a 15 g silica gel column using the same solvent system. The title compound is obtained as a yellow solid (0.73 g, 68% yield). ES+(m/z) 397 [M+H].

Workup

  1. washAfter eluting with methanol
  2. customto remove the salts, 20% 2.0 M NH3/MeOH)/EtOAC
  3. washto elute the product which

Sources & evidence

ORD record
ord-a6e4bdc6337d4698ad9f8eb9e50ef5dc
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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