2-Dimethylaminopyridine → HCID 178454163, compound

HRID 980233Notes

Reaction equation

HRID 980233 reaction equation
[O:1]=[C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[C:13]=1[NH:22][C:23]([C@@H:25]([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][CH:28]=1)=O)[CH2:3][C:4](=[O:11])[NH:5][C:6]1[S:7][CH:8]=[CH:9][N:10]=1.CN(C1C=CC=CN=1)C>O1CCCC1>[OH:1][C:2]1[C:12]2[C:13](=[C:14]([C:18]([F:19])([F:21])[F:20])[CH:15]=[CH:16][CH:17]=2)[N:22]=[C:23]([C@@H:25]([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:26][C:27]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[NH:29][CH:28]=2)[C:3]=1[C:4]([NH:5][C:6]1[S:7][CH:8]=[CH:9][N:10]=1)=[O:11]

Participants

4

Reactant 2

HCID 218852-DimethylaminopyridineHCID 54338439HCID 54338439, compound

Product 1

HCID 178454163HCID 178454163, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure of Step C of Example 7, a solution of 28 g of the product of Step B in 280 ml of tetrahydrofuran and 5.25 g of dimethylaminopyridine were reacted to obtain 16.9 g of 1,1-dimethylethyl N-[(S) 1-[4-hydroxy-3-[(2-thiazolylamino)-carbonyl]-8-(trifluoromethyl)-quinolin-2-yl]-2-(1H-indol-3-yl)-ethyl]-carbamate melting at 270° C. and having a specific rotation of [α]D =+33°±2° (c=0.5% in CH3COOH).

Sources & evidence

ORD record
ord-31d2cbf58a594d0bb0ae05fcf87b0d37
Source dataset
uspto-grants-1987_01
Patent number
US04636512

Reaction notes

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