Lithium Hydroxide → HCID 86694435, compound

HRID 1428261Notes

Reaction equation

HRID 1428261 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]([NH:21][CH2:22][C:23]4[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH:24]=4)=[O:20])[CH2:15][CH2:16][CH2:17]3)[CH2:12][CH2:11]2)=[N:3][CH:2]=1.[OH-].[Li+]>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]([NH:21][CH2:22][C:23]4[CH:24]=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:31][CH:32]=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 68052027HCID 68052027, compound

Product 1

HCID 86694435HCID 86694435, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To methyl 4-[({[(3aR,7aR)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)octahydro-4H-pyrrolo[3,2-b]pyridine-4-yl]carbonyl}amino)methyl]benzoate (TFA salt) from Example 23 (8.2 mg, 0.015 mmol) was added MeOH (75 μL) and aqueous lithium hydroxide (299 μL, 0.149 mmol, 2.0 M) solution at 22° C. The reaction was stirred for 18 hours before being concentrated and dissolved in DMSO (2.0 mL). The resulting solution was purified by mass triggered reverse phase HPLC. Lyophilization of the desired fractions gave the title compound (TFA salt). LRMS calc'd for C22H25N6O3 [M+H]+, 421; found 421. Jak1 activity: +.

Workup

  1. customat 22° C
  2. concentrationbefore being concentrated
  3. dissolutiondissolved in DMSO (2.0 mL)
  4. customThe resulting solution was purified by mass triggered reverse phase HPLC

Sources & evidence

ORD record
ord-8c10d1fbb80e4c07a7504c1d11bfd5d7
Source dataset
uspto-grants-2015_01
Patent number
US08937077B2

Reaction notes

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