Methanol → HCID 68859059, compound

HRID 1986198Notes

Reaction equation

HRID 1986198 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[CH:10][C:11]2[CH:15]=[C:14]([C:16]3[C:21]([CH3:22])=[CH:20][N:19]=[C:18]([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:17]=3)[S:13][C:12]=2[CH:34]=1)(C)(C)C.C(O)(C(F)(F)F)=O.CO>ClCCl>[NH2:7][C:8]1[CH:9]=[CH:10][C:11]2[CH:15]=[C:14]([C:16]3[C:21]([CH3:22])=[CH:20][N:19]=[C:18]([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:17]=3)[S:13][C:12]=2[CH:34]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 68857906HCID 68857906, compound

Product 1

HCID 68859059HCID 68859059, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-{5-Methyl-2-[3-(4-methylpiperazin-1-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophen-6-yl)-carbamic acid tert-butyl ester (0.33 g, 0.66 mmol) is dissolved in dichloromethane (6 mL) and TFA (0.78 mL) is added. The solution is stirred for 20 hours before adding methanol. The mixture is passed through an SCX column. After eluting with methanol, 20% of 2.0 M NH3/MeOH in EtOAc is used to elute the product which is then chromatographed on silica gel, eluting with 2.0 M NH3/MeOH in dichloromethane 0-15%, to give the title compound as a yellow oil. (166 mg, 64% yield). ES+(m/z) 397 [M+H].

Workup

  1. washAfter eluting with methanol, 20% of 2.0 M NH3/MeOH in EtOAc
  2. washto elute the product which
  3. customis then chromatographed on silica gel
  4. washeluting with 2.0 M NH3/MeOH in dichloromethane 0-15%

Sources & evidence

ORD record
ord-dd18d464272b4cb6b6209bdc8305d0bd
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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