4-[[2-[5-[[Boc(2-methoxyethyl)amino]methyl]-2-pyridyl]-7-thieno[3,2-b]pyridyl]oxy]-3-fluoroaniline → HCID 67048207, compound

HRID 1026837Notes

Reaction equation

HRID 1026837 reaction equation
[NH2:1][C:2]1[CH:36]=[CH:35][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[CH:13]=[C:14]([C:16]4[N:21]=[CH:20][C:19]([CH2:22][N:23]([CH2:31][CH2:32][O:33][CH3:34])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:18][CH:17]=4)[S:15][C:8]=23)=[C:4]([F:37])[CH:3]=1.[CH:38]1([S:41]([NH:44][C:45](=O)[O:46]CC)(=[O:43])=[O:42])[CH2:40][CH2:39]1>COCCOC.CCOC(C)=O.O>[CH:38]1([S:41]([NH:44][C:45](=[O:46])[NH:1][C:2]2[CH:36]=[CH:35][C:5]([O:6][C:7]3[CH:12]=[CH:11][N:10]=[C:9]4[CH:13]=[C:14]([C:16]5[N:21]=[CH:20][C:19]([CH2:22][N:23]([CH2:31][CH2:32][O:33][CH3:34])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:18][CH:17]=5)[S:15][C:8]=34)=[C:4]([F:37])[CH:3]=2)(=[O:43])=[O:42])[CH2:40][CH2:39]1

Participants

6

Reactant 2

HCID 579194724-[[2-[5-[[Boc(2-methoxyethyl)amino]methyl]-2-pyridyl]-7-thieno[3,2-b]pyridyl]oxy]-3-fluoroanilineHCID 58207628HCID 58207628, compound

Product 1

HCID 67048207HCID 67048207, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of the amine 126 (500 mg, 0.953 mmol) in DME (4 ml) was added the carbamate 374 (460 mg, 2.5 eq, 2.383 mmol) and the reaction mixture was heated to 120° C. for 1 day. The mixture was cooled to RT, diluted with EtOAc and water and the organic phase was collected, dried over Na2SO4, filtered and concentrated. Purification of the residue by column chromatography (eluent EtOAc to 50% Acetone in EtOAc) afforded 375 as a brown oil (130 mg, 55%). MS (m/z)=672.5 (M+H)

Workup

  1. temperatureThe mixture was cooled to RT
  2. customthe organic phase was collected
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification of the residue by column chromatography (eluent EtOAc to 50% Acetone in EtOAc)

Sources & evidence

ORD record
ord-adadecf16cc74405af1edf8cd10beac6
Source dataset
uspto-grants-2014_05
Patent number
US08729268B2

Reaction notes

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