Triethylamine → HCID 59410665, compound

HRID 912539Notes

Reaction equation

HRID 912539 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][NH:21][CH3:22])=[C:13]([C:23]([F:26])([F:25])[F:24])[CH:12]=3)[N:7]=[C:6]([C:27]#[N:28])[C:5]=2[N:4]=[CH:3]1.C(N(CC)CC)C.Cl.[CH3:37][N:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH:39]1[C:44]([OH:46])=O.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>C(Cl)Cl>[C:27]([C:6]1[C:5]2[N:4]=[CH:3][N:2]([CH3:1])[C:10]=2[CH:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][N:21]([CH3:22])[C:44]([CH:39]3[CH2:40][CH2:41][CH2:42][CH2:43][N:38]3[CH3:37])=[O:46])=[C:13]([C:23]([F:26])([F:24])[F:25])[CH:12]=2)[N:7]=1)#[N:28]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27782611-Methylpiperidine-2-carboxylic acid hydrochlorideHCID 59410673methyl-6-(4-(3-(methylamino)propoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

Product 1

HCID 59410665HCID 59410665, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-methyl-6-(4-(3-(methylamino)propoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile (50 mg), triethylamine (71 μL), 1-methylpiperidine-2-carboxylic acid hydrochloride (17 mg), and O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (58 mg) in DCM (1.5 ml) was stirred overnight at room temperature. The mixture was washed with sodium bicarbonate and then purified by prep HPLC (acidic) to give the expected product (11 mg). NMR (CD3OD) δ: 8.29-8.52 (m, 4H), 7.27-7.40 (m, 1H), 4.16-4.36 (m, 2H), 4.06 (s, 3H), 3.58-3.92 (m, 2H), 2.86-3.27 (m, 5H), 2.14-2.37 (m, 6H), 1.26-1.90 (m, 6H). MS m/z 515 (M+H).

Workup

  1. washThe mixture was washed with sodium bicarbonate
  2. custompurified by prep HPLC (acidic)

Sources & evidence

ORD record
ord-1378573da67044c881ab4075fad1e8e7
Source dataset
uspto-grants-2011_09
Patent number
US08026236B2

Reaction notes

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