Triethylamine → HCID 66707062, compound

HRID 911373Notes

Reaction equation

HRID 911373 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28](O)=[O:29])=[CH:24][CH:23]=3)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN.[CH2:34]([N:36](CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28](=[O:29])[NH:36][CH3:34])=[CH:24][CH:23]=3)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 6364545Methylamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57656359HCID 57656359, compound

Product 1

HCID 66707062HCID 66707062, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 3-(tert-butoxycarbonyl)-6-(4-carboxy-benzylamino)-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.1 g, 0.3 mmol), methylamine hydrochloride (31 mg, 0.46 mmol), triethylamine (0.1 g, 0.9 mmol), HATU (0.2 g, 0.5 mmol), anhydrous DMF (3 mL) and stir at ambient temperature for 17 h. Partition the reaction mixture between brine (5 mL) and diethyl ether (5 mL), separate the organic layer and dry over anhydrous Na2SO4. Evaporate the solvent to obtain 3-(tert-butoxycarbonyl)-7-chloro-6-(4-methylcarbamoyl-benzylamino)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow oil (0.1 g, 93%). MS (ES+) m/z: 344 (M+H−Boc)+.

Workup

  1. customPartition the reaction mixture between brine (5 mL) and diethyl ether (5 mL)
  2. customseparate the organic layer
  3. dry with materialdry over anhydrous Na2SO4
  4. customEvaporate the solvent

Sources & evidence

ORD record
ord-29d5ea49dca94a2ea6c7f72dbb475bcf
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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