Diisopropylethylamine → HCID 11591606, compound

HRID 2358022Notes

Reaction equation

HRID 2358022 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]([CH2:15][CH2:16][C:17]1[CH:18]=[N:19][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=1)[N:8]([CH:27]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:28]([OH:30])=O)[CH2:7][CH2:6]2.Cl.CN.C1C[N:43]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)[CH2:42]C1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CC(=O)OCC.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]([CH2:15][CH2:16][C:17]1[CH:18]=[N:19][C:20]([C:23]([F:25])([F:26])[F:24])=[CH:21][CH:22]=1)[N:8]([CH:27]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:28]([NH:43][CH3:42])=[O:30])[CH2:7][CH2:6]2

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 6364545Methylamine hydrochlorideHCID 59389629HCID 59389629, compound

Product 1

HCID 11591606HCID 11591606, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of {6,7-dimethoxy-1-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-3,4-dihydro-1H-isoquinolin-2-yl}-phenyl-acetic acid (0.20 mmol), methylamine hydrochloride (0.20 mmol), PyBOP (0.20 mmol) and DIPEA (0.46 mmol) in DMF (1.0 mL) is stirred at RT for 20 h. Water and EA are added, the layers are separated and the aqueous layer is extracted with EA. The combined organic extracts are dried over MgSO4 and concentrated in vacuo. The residue is purified by flash chromatography (EA) to give the desired product as a viscous oil.

Workup

  1. customthe layers are separated
  2. extractionthe aqueous layer is extracted with EA
  3. dry with materialThe combined organic extracts are dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash chromatography (EA)

Sources & evidence

ORD record
ord-0904d34e2ad049daa8d41916ae108355
Source dataset
uspto-grants-2010_07
Patent number
US07763638B2

Reaction notes

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