Formic Acid → 3(R)-[3-(4'-cyanobiphenyl-4-yl)-1H-pyrrol-1yl]-N-[2,2-dimethyl-1(S)-(pyridin-4-ylcarbamoyl)propyl]succinamic acid formate salt

HRID 382165Notes

Reaction equation

HRID 382165 reaction equation
C([O:8][C:9](=[O:48])[CH2:10][C@@H:11]([N:29]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][C:37]([C:40]3[CH:45]=[CH:44][C:43]([C:46]#[N:47])=[CH:42][CH:41]=3)=[CH:36][CH:35]=2)=[CH:30]1)[C:12]([NH:14][C@H:15]([C:20](=[O:28])[NH:21][C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)[C:16]([CH3:19])([CH3:18])[CH3:17])=[O:13])C1C=CC=CC=1.C(O)=O>[Pd].CO>[CH:9]([OH:48])=[O:8].[C:46]([C:43]1[CH:42]=[CH:41][C:40]([C:37]2[CH:38]=[CH:39][C:34]([C:31]3[CH:32]=[CH:33][N:29]([C@@H:11]([C:12]([NH:14][C@H:15]([C:20](=[O:28])[NH:21][C:22]4[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=4)[C:16]([CH3:19])([CH3:18])[CH3:17])=[O:13])[CH2:10][C:9]([OH:48])=[O:8])[CH:30]=3)=[CH:35][CH:36]=2)=[CH:45][CH:44]=1)#[N:47]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 154596793(R)-[3-(4'-cyanobiphenyl-4-yl)-1H-pyrrol-1-yl]-N-[2,2-dimethyl-1(S)-(pyridin-4-ylcarbamoyl)propyl]succinamic acid benzyl ester

Product 1

HCID 701425613(R)-[3-(4'-cyanobiphenyl-4-yl)-1H-pyrrol-1yl]-N-[2,2-dimethyl-1(S)-(pyridin-4-ylcarbamoyl)propyl]succinamic acid formate saltYield 89.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of palladium on carbon and 3(R)-[3-(4′-cyanobiphenyl-4-yl)-1 H-pyrrol-1-yl]-N-[2,2-dimethyl-1(S)-(pyridin-4-ylcarbamoyl)propyl]succinamic acid benzyl ester (72 mg, 0.112 mmol) in MeOH with formic acid afforded 30 mg (49%) of 3(R)-[3-(4′-cyanobiphenyl-4-yl)-1H-pyrrol-1yl]-N-[2,2-dimethyl-1(S)-(pyridin4-ylcarbamoyl)propyl]succinamic acid formate salt as a solid, mp 134-6° C.

Sources & evidence

ORD record
ord-1798fc8fb70e4ab3a1b3815ec03033a5
Source dataset
uspto-grants-2001_10
Patent number
US06306892B1

Reaction notes

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