Dimethylamine → HCID 67305329, compound

HRID 1921984Notes

Reaction equation

HRID 1921984 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[CH:9]=[C:8]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH3:25])[N:19]=2)[CH:7]=1)=[O:4].[CH3:26][NH:27][CH3:28]>CN(C)C(=O)C>[CH3:26][N:27]([CH3:28])[CH2:2][C:3]([NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[CH:9]=[C:8]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH3:25])[N:19]=2)[CH:7]=1)=[O:4]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 58336389HCID 58336389, compound

Product 1

HCID 67305329HCID 67305329, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-chloro-N-(7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl)acetamide 34 (0.125 mg, 0.35 mmol) in N,N-dimethylacetamide (1 mL), dimethylamine (1.5 mL, 2M solution in methanol, 3 mmol) was added. The reaction mixture was stirred at 60° C. overnight. The crude reaction mixture was concentrated under high vacuum and which was purified by reverse phase chromatography on preparative LC/UV/MS system using a mass triggered fractionation. Compound was eluted from the HPLC column (Maccel 120-10-C18 SH 10 μm 20 mmID×50 mm) at 88 mL/min with acetonitrile/water gradient using 0.1% FA as a modifier. 2-(dimethylamino)-N-(7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl)acetamide 137 was isolated as a yellow-orange solid (0.050 g). M.p.=70-73° C. 400 MHz 1H NMR (DMSO-d6) δ: 9.96 (s, 1H), 8.49 (s, 1H), 8.38 (s, 2H), 8.01 (d, J=8.6 Hz, 1H), 7.29-7.14 (m, 4H), 3.92 (s, 3H), 3.24 (s, 2H), 2.90 (br s, 3H), 2.42 (s, 6H); Experimental Elemental Analysis (0.13 equivalents of water)=65.32% C, 6.36% H, 18.75% N; Calculated Elemental Analysis 65.32% C, 6.37% H, 19.04% N; LCMS (m/z): 367 [M+H].

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated under high vacuum and which
  3. customwas purified by reverse phase chromatography on preparative LC/UV/MS system
  4. washCompound was eluted from the HPLC column (Maccel 120-10-C18 SH 10 μm 20 mmID×50 mm) at 88 mL/min with acetonitrile/water gradient

Sources & evidence

ORD record
ord-d36e5b629b5d464d90e9b0ae8ac95cda
Source dataset
uspto-grants-2012_05
Patent number
US08173808B2

Reaction notes

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