Dimethylamine, hydrochloride → HCID 66829143, compound

HRID 1046490Notes

Reaction equation

HRID 1046490 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[C:13]3[C:14]([C:36]4[CH:41]=[CH:40][N:39]=[C:38]([C:42](O)=[O:43])[CH:37]=4)=[N:15][N:16]([C:17]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:12]=3[CH:11]=[CH:10][N:9]=2)[CH2:3][CH2:2]1.Cl.[CH3:46][NH:47][CH3:48].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O.C(OCC)(=O)C>[CH3:46][N:47]([CH3:48])[C:42](=[O:43])[C:38]1[CH:37]=[C:36]([C:14]2[C:13]3[C:8]([O:7][CH:4]4[CH2:3][CH2:2][O:1][CH2:6][CH2:5]4)=[N:9][CH:10]=[CH:11][C:12]=3[N:16]([C:17]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:15]=2)[CH:41]=[CH:40][N:39]=1

Participants

8

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66825690HCID 66825690, compound

Product 1

HCID 66829143HCID 66829143, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4-(4-(tetrahydro-2H-pyran-4-yloxy)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)picolinic acid (100 mg, 0.17 mmole), dimethylamine hydrochloride (30 mg, 0.34 mmole), HATU (100 mg, 0.26 mole), DIPEA (0.2 mL) in DMF (20 mL) was stirred overnight at 25° C. Ethyl acetate (100 mL) and water (50 mL) were added. The organic layer was separated and washed with water (30 mL) and brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give the crude desired product as a yellowish oil (70 mg, 68%). LCMS (Method A): m/z=610 [M+H]+; 2.33 min.

Workup

  1. customThe organic layer was separated
  2. washwashed with water (30 mL) and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cb90b20fdd2f444984ac2fd9f31ea17b
Source dataset
uspto-grants-2013_10
Patent number
US08569281B2

Reaction notes

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