Lithium Hydroxide → HCID 56967573, compound

HRID 1428255Notes

Reaction equation

HRID 1428255 reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([N:10]2[C@H:18]3[C@H:13]([N:14]([C:19]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][C:26]([C:29]([O:31]C)=[O:30])=[CH:25][CH:24]=4)=[O:20])[CH2:15][CH2:16][CH2:17]3)[CH2:12][CH2:11]2)=[N:3][CH:2]=1.[Li+].[OH-]>CO>[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([N:10]2[C@H:18]3[C@H:13]([N:14]([C:19]([O:21][CH2:22][C:23]4[CH:24]=[CH:25][C:26]([C:29]([OH:31])=[O:30])=[CH:27][CH:28]=4)=[O:20])[CH2:15][CH2:16][CH2:17]3)[CH2:12][CH2:11]2)=[N:3][CH:2]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86694433HCID 86694433, compound

Product 1

HCID 56967573HCID 56967573, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of the product of Step 1 (11 mg, 0.025 mmol) in MeOH (0.13 mL) was added 0.5 M aqueous LiOH (0.51 mL, 0.25 mmol) and the reaction mixture was stirred for 48 hours at ambient temperature. The reaction mixture was concentrated in vacuo and purified by mass triggered reverse phase HPLC. Lyophilization of the desired fractions afforded the title product (TFA salt) as a white solid. LRMS calc'd for C22H24N5O4 [M+H]+, 422; found 422. Jak1 activity: +.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by mass triggered reverse phase HPLC

Sources & evidence

ORD record
ord-b4c4cf037ace4b1a9af460c68c8beb31
Source dataset
uspto-grants-2015_01
Patent number
US08937077B2

Reaction notes

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