Diisopropylethylamine → HCID 67145291, compound

HRID 912536Notes

Reaction equation

HRID 912536 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]([OH:9])=O.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:43][N:44]1[C:52]2[CH:51]=[C:50]([C:53]3[CH:58]=[CH:57][C:56]([O:59][CH2:60][CH2:61][NH:62][CH3:63])=[C:55]([C:64]([F:67])([F:66])[F:65])[CH:54]=3)[N:49]=[C:48]([C:68]#[N:69])[C:47]=2[N:46]=[CH:45]1>ClCCl>[C:68]([C:48]1[C:47]2[N:46]=[CH:45][N:44]([CH3:43])[C:52]=2[CH:51]=[C:50]([C:53]2[CH:58]=[CH:57][C:56]([O:59][CH2:60][CH2:61][N:62]([CH3:63])[C:7]([C@@H:3]3[CH2:4][CH2:5][CH2:6][N:2]3[CH3:1])=[O:9])=[C:55]([C:64]([F:67])([F:65])[F:66])[CH:54]=2)[N:49]=1)#[N:69]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 643474N-Methyl-L-prolineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59410639HCID 59410639, compound

Product 1

HCID 67145291HCID 67145291, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-1-methylpyrrolidine-2-carboxylic acid (16 mg), DIPEA (60 ul) and HBTU (51.7 mg) in dichloromethane (2 ml) was added 1-methyl-6-(4-(2-(methylamino)ethoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile (51.1 mg). The reaction was left stirring at room temperature for 60 hrs. Reaction mixture was diluted with dichloromethane, washed with sodium bicarbarbonate and water. Organic layer was dried over magnesium sulphate and solvent removed under reduced pressure. The residue was purified by acidic prep HPLC and cationic ion exchange column to yield (S)—N-(2-(4-(4-cyano-1-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)ethyl)-N,1-dimethylpyrrolidine-2-carboxamide (30.2 mg).

Workup

  1. waitThe reaction was left
  2. customReaction mixture
  3. washwashed with sodium bicarbarbonate and water
  4. dry with materialOrganic layer was dried over magnesium sulphate and solvent
  5. customremoved under reduced pressure
  6. customThe residue was purified by acidic prep HPLC and cationic ion exchange column

Sources & evidence

ORD record
ord-14291082e58244a989c3ae77f9122e75
Source dataset
uspto-grants-2011_09
Patent number
US08026236B2

Reaction notes

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