4-Hydroxypyrrolidine → HCID 66612325, compound

HRID 2064382Notes

Reaction equation

HRID 2064382 reaction equation
[C:1]([C:3]1[C@@H:8]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=2[S:17]([CH3:20])(=[O:19])=[O:18])[N:7]([C:21](OC2C=CC([N+]([O-])=O)=CC=2)=[O:22])[C:6](=[O:33])[N:5]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:43])([F:42])[F:41])[CH:35]=2)[C:4]=1[CH3:44])#[N:2].[NH:45]1[CH2:49][CH2:48][CH:47]([OH:50])[CH2:46]1>C(#N)C>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([C@@H:8]2[C:3]([C:1]#[N:2])=[C:4]([CH3:44])[N:5]([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:42])([F:43])[F:41])[CH:35]=3)[C:6](=[O:33])[N:7]2[C:21]([N:45]2[CH2:49][CH2:48][CH:47]([OH:50])[CH2:46]2)=[O:22])=[C:10]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:11]=1)#[N:16]

Participants

4

Reactant 2

HCID 982104-HydroxypyrrolidineHCID 666017634-Nitrophenyl (6S)-5-cyano-6-[4-cyano-2-(methylsulfonyl)phenyl]-4-methyl-2-oxo-3-[3-(trifluoromethyl)phenyl]-3,6-dihydropyrimidine-1(2H)-carboxylate

Product 1

HCID 66612325HCID 66612325, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

According to the General Procedure 1, 4-nitrophenyl (6S)-5-cyano-6-[4-cyano-2-(methylsulfonyl)phenyl]-4-methyl-2-oxo-3-[3-(trifluoromethyl)phenyl]-3,6-dihydropyrimidine-1(2H)-carboxylate (78.0 mg, 0.125 mmol; Example 6A) was reacted with pyrrolidin-3-ol (32.6 mg, 0.374 mmol) in acetonitrile (1 ml) to give the target compound (58 mg, 81% of theory).

Workup

  1. customto give the target compound (58 mg, 81% of theory)

Sources & evidence

ORD record
ord-9742e7b7904e4eb38418cd7afc8fa562
Source dataset
uspto-grants-2012_10
Patent number
US08288402B2

Reaction notes

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