Diisopropylethylamine → HCID 57717943, compound

HRID 1984825Notes

Reaction equation

HRID 1984825 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:22]=[CH:21][C:6]([O:7][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[N:13][C:12]([C:18]([OH:20])=O)=[CH:11]3)=[CH:5][CH:4]=1.Cl.[CH3:26][O:27][C:28](=[O:46])[C@@H:29]([NH2:45])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][C:40]([F:43])=[C:39]([Cl:44])[CH:38]=2)=[CH:33][CH:32]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:26][O:27][C:28](=[O:46])[C@@H:29]([NH:45][C:18]([C:12]1[N:13]=[CH:14][C:15]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:7][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:24])([F:23])[F:1])=[CH:22][CH:21]=1)=[CH:17][CH:16]=2)=[O:20])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][C:40]([F:43])=[C:39]([Cl:44])[CH:38]=2)=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68868239HCID 68868239, compoundHCID 68869261HCID 68869261, compound

Product 1

HCID 57717943HCID 57717943, compoundYield 26.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-(4-trifluoromethyl-phenoxy)-isoquinoline-3-carboxylic acid (0.050 g, 0.149 mmol) in DMF (2.0 mL) was treated with 2(S)-amino-3-(3′-chloro-4′-fluoro-biphenyl-4-yl)-propionic acid methyl ester hydrochloride (0.051 g, 0.164 mmol), HBTU (0.062 g, 0.164 mmol), and DIEA (0.112 mL) by the general procedure A. The crude product was purified by flash column chromatography on silica gel using Hexanes:EtOAc 88:12 to give 0.025 g of 3-(3′-Chloro-4′-fluoro-biphenyl-4-yl)-(2S)-{[6-(4-trifluoromethyl-phenoxy)-isoquinoline-3-carbonyl]-amino}-propionic acid methyl ester.

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-0b36ec87325c4c15a0fbffed2ed7203c
Source dataset
uspto-grants-2009_06
Patent number
US07544699B2

Reaction notes

Loading…