Triethylamine → HCID 136401941, compound

HRID 1064166Notes

Reaction equation

HRID 1064166 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=[CH:15][C:16](=[O:32])[NH:17][C:18]2[CH:19]=[C:20]3[C:30](=[O:31])[NH:29][N:28]=[CH:27][C:22]4=[CH:23][NH:24][C:25]([CH:26]=2)=[C:21]34)[CH2:10][CH2:9]1)=O)(C)(C)C.C(OC(N1CCC(C=[CH:47][C:48]([OH:50])=[O:49])CC1)=O)(C)(C)C.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O>[C:48]([OH:50])(=[O:49])[CH3:47].[O:31]=[C:30]1[C:20]2[C:21]3[C:22](=[CH:23][NH:24][C:25]=3[CH:26]=[C:18]([NH:17][C:16](=[O:32])[CH:15]=[CH:14][CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH:19]=2)[CH:27]=[N:28][NH:29]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 54360779HCID 54360779, compoundHCID 136411687HCID 136411687, compound

Product 1

HCID 136401941HCID 136401941, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Preparation of intermediate 146(a) from the title compound of Example 2 (freebase) (49 mg, 0.245 mmol), 4-(2-carboxy-vinyl)-piperidine-1-carboxylic acid tert-butyl ester (99 mg, 0.39 mmol), triethylamine (0.069 mL, 0.49 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (148 mg, 0.39 mmol) in N,N-dimethylformamide (3 mL) was carried out analogously to Example 11. Silica gel chromatography (eluted with 10% methanol in CH2Cl2), also in an analogous manner, afforded Intermediate 146(a) (58 mg, 0.13 mmol) as a yellow powder in 55% yield.

Sources & evidence

ORD record
ord-f2f4ae9296c6466fa6fddbc68b8313fc
Source dataset
uspto-grants-2005_11
Patent number
US06967198B2

Reaction notes

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