Potassium Carbonate → HCID 89544992, compound

HRID 2283423Notes

Reaction equation

HRID 2283423 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:11][C@@H:12]([CH3:17])[CH2:13][C:14]([NH2:16])=[O:15])[CH2:9][CH3:10])=[C:4]([F:18])[C:3]=1[C:19]([C:21]1[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=1)=[O:20].C([O-])([O-])=[O:30].[K+].[K+]>CS(C)=O>[C:14]([CH2:13][C@@H:12]([NH:11][C@@H:8]([C:5]1[C:4]([F:18])=[C:3]([C:19]([C:21]2[CH:22]=[CH:23][C:24]([C:27]([NH2:28])=[O:30])=[CH:25][CH:26]=2)=[O:20])[C:2]([Cl:1])=[CH:7][CH:6]=1)[CH2:9][CH3:10])[CH3:17])(=[O:15])[NH2:16]

Participants

4

Reactant 2

HCID 11430Potassium Carbonate2×HCID 89544492HCID 89544492, compound

Product 1

HCID 89544992HCID 89544992, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To (3S)-3-{[(1R)-1-{4-chloro-3-[(4-cyanophenyl)carbonyl]-2-fluorophenyl}propyl]amino}-butanamide (compound of Example 91) (0.016 g, 0.04 mmol) added DMSO (1 ml) treated with K2CO3 (0.027 g, 0.2 mmol) stirred ambient for 2 hours, further K2CO3 (0.027 g, 0.2 mmol) added left stirring ambient for 16 hours. Reaction purified by Prep HPLC to give 4-({3-[(1R)-1-{[(2S)-1-carbamoylpropan-2-yl]amino}propyl]-6-chloro-2-fluorophenyl}carbonyl)-benzamide (1 mg).

Workup

  1. waitleft
  2. stirringstirring ambient for 16 hours
  3. customReaction
  4. custompurified by Prep HPLC

Sources & evidence

ORD record
ord-58bde38d999e41098fa29d5d75374916
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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