Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamate → HCID 178502017, compound

HRID 241201Notes

Reaction equation

HRID 241201 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[C:10]([N:15]3[CH2:21][C:20]4[CH:22]=[C:23]([C:26]5[N:31]=[C:30]([NH2:32])[C:29]([NH2:33])=[CH:28][CH:27]=5)[CH:24]=[CH:25][C:19]=4[O:18][CH2:17][CH2:16]3)=[N:11][CH:12]=[N:13][CH:14]=2)=[CH:4][CH:3]=1.[CH3:34][O:35][C:36]([NH:38][C:39](=NC(OC)=O)SC)=[O:37]>C(O)(=O)C.C(OCC)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[C:10]([N:15]3[CH2:21][C:20]4[CH:22]=[C:23]([C:26]5[N:31]=[C:30]6[NH:32][C:39]([NH:38][C:36](=[O:37])[O:35][CH3:34])=[N:33][C:29]6=[CH:28][CH:27]=5)[CH:24]=[CH:25][C:19]=4[O:18][CH2:17][CH2:16]3)=[N:11][CH:12]=[N:13][CH:14]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 66820522HCID 66820522, compound

Product 1

HCID 178502017HCID 178502017, compoundYield 304.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-(4-{5-[(4-fluorophenyl)methyl]pyrimidin-4-yl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)pyridine-2,3-diamine (0.200 g, 0.438 mmol) in glacial acetic acid (3 mL) was added 1,3-bis(methoxycarbonyl)-2-methyl-2-thiopseudourea (0.117 g, 0.570 mmol). The reaction mixture was stirred at 80° C. for 2 h and then concentrated. Ethyl acetate (100 mL) was added to the residue, and the solution was washed with saturated sodium bicarbonate (50 mL) then dried over anhydrous sodium sulfate. Filtration and concentration afforded a brown residue that was taken up in diethyl ether (10 mL) and the resulting precipitate was collected by filtration to give methyl [5-(4-{5-[(4-fluorophenyl)methyl]pyrimidin-4-yl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-3H-imidazo[4,5-b]pyridine-2-yl]carbamate (0.70 g, 30% yield) as a brown solid. MS (EI) for C26H25FN6O: 457 (MH+).

Workup

  1. concentrationconcentrated
  2. additionEthyl acetate (100 mL) was added to the residue
  3. washthe solution was washed with saturated sodium bicarbonate (50 mL)
  4. dry with materialthen dried over anhydrous sodium sulfate
  5. filtrationFiltration and concentration
  6. customafforded a brown residue that
  7. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-637cca7f0dad414dbc2fbf6bb72cc232
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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