Water → HCID 59589532, compound

HRID 1054396Notes

Reaction equation

HRID 1054396 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[N:22]3[N:23]=[C:24]([NH:26][C:27]4[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][N:36]5[CH2:40][CH2:39][CH2:38][CH2:37]5)=[CH:29][CH:28]=4)[N:25]=[C:21]3[CH:20]=[CH:19][CH:18]=2)[CH:12]=1)C.O>C(OCC)C>[N:36]1([CH2:35][CH2:34][O:33][C:30]2[CH:29]=[CH:28][C:27]([NH:26][C:24]3[N:25]=[C:21]4[CH:20]=[CH:19][CH:18]=[C:17]([C:13]5[CH:12]=[C:11]([CH2:10][OH:9])[CH:16]=[CH:15][CH:14]=5)[N:22]4[N:23]=3)=[CH:32][CH:31]=2)[CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 59589941HCID 59589941, compound

Product 1

HCID 59589532HCID 59589532, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a slurry of lithium aluminium hydride (82.6 mg, 2.12 mmol) in diethylether (10 mL) was added 3-{2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl}-benzoic acid ethyl ester (0.50 g, 1.06 mmol) portionwise. The mixture was stirred at room temperature for 6 hrs. Water was added to quench the hydride and the aqueous layer was removed. The organic layer was concentrated in vacuo, and the crude product loaded onto an SCX column, which was washed with methanol and the product eluted with 2M ammonia in methanol, then concentrated in vacuo. Yield: 0.35 g, 76%. A small amount was purified by preparatory HPLC. RT: 2.32, MI: 430, Method: 2.

Workup

  1. customto quench the hydride
  2. customthe aqueous layer was removed
  3. concentrationThe organic layer was concentrated in vacuo
  4. washwas washed with methanol
  5. washthe product eluted with 2M ammonia in methanol
  6. concentrationconcentrated in vacuo
  7. customA small amount was purified by preparatory HPLC
  8. customRT

Sources & evidence

ORD record
ord-42f38c10d6294d499a700983d1b10912
Source dataset
uspto-grants-2016_07
Patent number
US09394301B2

Reaction notes

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