Dimethylamine, hydrochloride → HCID 66971288, compound

HRID 1361299Notes

Reaction equation

HRID 1361299 reaction equation
[C:1]([N:8]1[CH2:15][C@@H:14]([N:16]([CH:23]2[CH2:28][CH2:27][C:26]([CH3:30])([CH3:29])[CH2:25][CH2:24]2)[C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:13][C@H:9]1[C:10](O)=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C[CH2:32][N:33](C(C)C)[CH:34](C)C.Cl.CNC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:1]([N:8]1[CH2:15][C@@H:14]([N:16]([CH:23]2[CH2:28][CH2:27][C:26]([CH3:30])([CH3:29])[CH2:25][CH2:24]2)[C:17](=[O:22])[C:18]([CH3:20])([CH3:19])[CH3:21])[CH2:13][C@H:9]1[C:10]([N:33]([CH3:34])[CH3:32])=[O:11])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

6

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66971349HCID 66971349, compound

Product 1

HCID 66971288HCID 66971288, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (4S)-1-BOC-4-[(4,4-dimethylcyclohexyl)(2,2-dimethylpropanoyl)amino]-L-proline (0.93 g, 2.2 mmol) prepared in Step C in DMF (10□) was added dropwise DIPEA (0.95□, 5.5 mmol) followed by dimethylamine-HCl salt (0.21 g, 2.57 mmol) and HBTU (0.83 g, 2.2 mmol). The reaction solution was stirred at rt for 2 h, and concentrated in vacuo. The residue was diluted with EtOAc, washed with a saturated NaHCO3 aqueous solution, water and 1N HCl. The organic solution was dried over MgSO4, concentrated in vacuo, and the residue was purified by column chromatography (eluent: EtOAc:Hex=2/1) to give the title compound (0.92 g, 93%).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with EtOAc
  3. washwashed with a saturated NaHCO3 aqueous solution, water and 1N HCl
  4. dry with materialThe organic solution was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customthe residue was purified by column chromatography (eluent: EtOAc:Hex=2/1)

Sources & evidence

ORD record
ord-a9d137b5a77445f49a129406d6448bcc
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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