Hydrochloric Acid → HCID 86640347, compound

HRID 1806842Notes

Reaction equation

HRID 1806842 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3](O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([C:39]#[N:40])[CH:19]([CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[NH:18][CH:17]([C:25](O)=[O:26])[CH:16]2[C:28]2[CH:33]=[CH:32][C:31](C(F)(F)F)=[C:30]([Cl:38])[CH:29]=2)=C(F)[CH:10]=1.CC1(C)[O:47][C@@H:46]([CH2:48][CH2:49][NH2:50])[CH2:45][O:44]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.[F:69][P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl>C(Cl)Cl.O1CCCC1>[OH:47][C@H:46]([CH2:45][OH:44])[CH2:48][CH2:49][NH:50][C:25]([CH:17]1[CH:16]([C:28]2[CH:33]=[CH:32][C:31]([F:69])=[C:30]([Cl:38])[CH:29]=2)[C:15]([C:12]2[CH:13]=[CH:14][C:9]([Cl:8])=[CH:10][C:3]=2[C:2]([F:7])([F:6])[F:1])([C:39]#[N:40])[CH:19]([CH2:20][C:21]([CH3:23])([CH3:24])[CH3:22])[NH:18]1)=[O:26]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 282937772-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethan-1-amineHCID 86640346HCID 86640346, compound

Product 1

HCID 86640347HCID 86640347, compoundYield 73%

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)-4-(4-chloro-2-fluoro-phenyl)-3-(3-chloro-4-trifluoromethyl-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid trifluoroacetic acid prepared in Example 71c (0.22 g, 0.35 mmol) was reacted with 2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethylamine (0.15 g, 1.05 mmol), HATU (0.24 g, 0.63 mmol) and iPr2NEt (0.3 mL, 1.74 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-(3-chloro-4-fluoro-phenyl)-4-(4-chloro-2-trifluoromethyl-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid ((S)-3,4-dihydroxy-butyl)-amide as a white solid (0.14 g, 73%).

Sources & evidence

ORD record
ord-a5a8d3013a4144088fca7d44cd314c5c
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

Loading…