Hydrochloric Acid → HCID 86640345, compound

HRID 1806838Notes

Reaction equation

HRID 1806838 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=O.[Br:8][C:9]1[CH:10]=[C:11]([CH:14]2[C:18]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[F:28])([C:19]#[N:20])[CH:17]([CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])[NH:16][CH:15]2[C:34](O)=[O:35])[S:12][CH:13]=1.[CH2:37]([NH2:39])[CH3:38].CN(C([O:47]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl>C(Cl)Cl.O1CCCC1>[OH:47][C@H:2]([CH2:3][OH:5])[CH2:38][CH2:37][NH:39][C:34]([CH:15]1[CH:14]([C:11]2[S:12][CH:13]=[C:9]([Br:8])[CH:10]=2)[C:18]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[F:28])([C:19]#[N:20])[CH:17]([CH2:29][C:30]([CH3:33])([CH3:31])[CH3:32])[NH:16]1)=[O:35]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6341EthylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86640344HCID 86640344, compound

Product 1

HCID 86640345HCID 86640345, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to the method described in Examples 42c, 42d, rac-(2R,3R,4R,5S)-3-(4-bromo-thiophen-2-yl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid trifluoroacetic acid prepared in Example 70c (0.2 g, 0.33 mmol) was reacted with 2-4S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethylamine (0.14 g, 1 mmol), HATU (0.22 g, 0.58 mmol) and iPr2NEt (0.28 mL, 1.63 mmol) in CH2Cl2 at room temperature for 20 h, then reacted with aqueous HCl solution in tetrahydrofuran at room temperature for 2 h to give rac-(2R,3R,4R,5S)-3-(4-bromo-thiophen-2-yl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid ((S)-3,4-dihydroxy-butyl)-amide as a white solid (0.15 g, 80%).

Sources & evidence

ORD record
ord-31686f2109474183895d65c34b5b90f4
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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