Water → HCID 66631463, compound

HRID 714483Notes

Reaction equation

HRID 714483 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:11]=[C:12]([C:16]([NH:18][CH3:19])=[O:17])[CH:13]=[CH:14][CH:15]=2)[C:5]([C:20]#[N:21])=[C:4]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][OH:31])=[CH:24][CH:23]=2)[C:3]=1[C:32]#[N:33].[NH:34]1[CH2:38][CH2:37][C@@H:36]([OH:39])[CH2:35]1.O>O1CCCC1>[C:20]([C:5]1[C:6]([S:8][CH2:9][C:10]2[CH:11]=[C:12]([C:16]([NH:18][CH3:19])=[O:17])[CH:13]=[CH:14][CH:15]=2)=[N:7][C:2]([N:34]2[CH2:38][CH2:37][C@@H:36]([OH:39])[CH2:35]2)=[C:3]([C:32]#[N:33])[C:4]=1[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][OH:31])=[CH:24][CH:23]=1)#[N:21]

Participants

5

Reactant 3

HCID 962WaterHCID 2759337(R)-3-PyrrolidinolHCID 86691915HCID 86691915, compound

Product 1

HCID 66631463HCID 66631463, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

73 mg (0.15 mmol) of 3-[({6-chloro-3,5-dicyano-4-[4-(2-hydroxyethoxy)phenyl]pyridin-2-yl}sulfanyl)methyl]-N-methylbenzenecarboxamide Example 84A were initially charged in 1.5 ml of tetrahydrofuran. After addition of 26.6 mg (0.31 mmol) of (R)-3-pyrrolidinol, the mixture was stirred at RT for 30 min. Water was added to the reaction mixture until a clear solution had formed. The solution was purified by preparative HPLC (Chromasil, water/acetonitrile+0.1% trifluoroacetic acid).

Workup

  1. customhad formed
  2. customThe solution was purified by preparative HPLC (Chromasil, water/acetonitrile+0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-63b0d91424dc4dc5b2c3791c79f3f51c
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

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