Piperidine-1-propylamine → HCID 68407389, compound

HRID 888030Notes

Reaction equation

HRID 888030 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[C:11]([O:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][C:26](=[O:46])[C:27]1[CH:32]=[CH:31][C:30]([C:33]2[C:34]3[S:45][CH:44]=[CH:43][C:35]=3[N:36]=[C:37](S(C)(=O)=O)[N:38]=2)=[CH:29][CH:28]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12]>CN(C)C(=O)C>[C:11]([O:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][C:26](=[O:46])[C:27]1[CH:32]=[CH:31][C:30]([C:33]2[C:34]3[S:45][CH:44]=[CH:43][C:35]=3[N:36]=[C:37]([NH:1][CH2:2][CH2:3][CH2:4][N:5]3[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]3)[N:38]=2)=[CH:29][CH:28]=1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 19049Piperidine-1-propylamineHCID 68408299HCID 68408299, compound

Product 1

HCID 68407389HCID 68407389, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 3-aminopropylpiperidine (60 μl, 0.38 mmol) and N-(2-t-butoxycarbonylaminophenyl)-4-[2-(methylsulfonyl)thieno[3,2-d]pyrimidin-4-yl]benzamide (Method 54, 81 mg, 0.15 mmol) in N,N-dimethylacetamide was heated first to 50° C. for 23 hours and then further heated to 75° C. for a period of 16 hours. The reaction mixture was evaporated to dryness and the crude residue purified by flash chromatography, on silica (10 g), eluting with methanol/dichloromethane (0-15%) to give the title compound (23 mg, 26%); Mass Spectrum: M+H+ 587.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe crude residue purified by flash chromatography, on silica (10 g)
  3. washeluting with methanol/dichloromethane (0-15%)

Sources & evidence

ORD record
ord-1c82662e06514bd785f8df600c8c2d89
Source dataset
uspto-grants-2012_08
Patent number
US08247562B2

Reaction notes

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