Trifluoroacetic acid → HCID 178511780, compound

HRID 980234Notes

Reaction equation

HRID 980234 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C@@H:16]([NH:27]C(=O)OC(C)(C)C)[CH2:17][C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)[C:3]=1[C:35]([NH:37][C:38]1[S:39][CH:40]=[CH:41][N:42]=1)=[O:36].FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:27][C@H:16]([C:4]1[C:3]([C:35]([NH:37][C:38]2[S:39][CH:40]=[CH:41][N:42]=2)=[O:36])=[C:2]([OH:1])[C:11]2[C:6](=[C:7]([C:12]([F:13])([F:15])[F:14])[CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178454163HCID 178454163, compound

Product 1

HCID 178511780HCID 178511780, compoundYield 116.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 16.9 g of product of Example 11, 170 ml of methylene chloride and 85 ml of trifluoroacetic acid was stirred for 3 hours at ambient temperature and the solvents were eliminated under reduced pressure. The crude oil residue was crystallized from ether and after filtering, rinsing and drying under reduced pressure at 50° C., 16.4 g of 2-[(S) 1-amino-2-(1H-indol-3-yl)-ethyl]-4-hydroxy-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline carboxamide were obtained in the form of trifluoroacetate melting at about 190° C.

Workup

  1. customThe crude oil residue was crystallized from ether
  2. filtrationafter filtering
  3. washrinsing
  4. customdrying under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-8080e5775a824ed28964f380d7bc8e47
Source dataset
uspto-grants-1987_01
Patent number
US04636512

Reaction notes

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