HCID 58529892, compound → HCID 58529976, compound

HRID 1972947Notes

Reaction equation

HRID 1972947 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:25]3[CH:26]=[CH:27][C:28]4[C:32]([CH:33]=3)=[N:31][N:30]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH:29]=4)[CH:9]=[C:10]([CH:11]3[CH2:14][N:13](C(OCC4C=CC=CC=4)=O)[CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1>Cl>[NH:13]1[CH2:14][CH:11]([C:10]2[N:6]3[C:7]([C:2]([NH2:1])=[N:3][CH:4]=[N:5]3)=[C:8]([C:25]3[CH:26]=[CH:27][C:28]4[C:32]([CH:33]=3)=[N:31][N:30]([CH2:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:29]=4)[CH:9]=2)[CH2:12]1

Participants

3

Reactant 1

HCID 58529892HCID 58529892, compound

Product 1

HCID 58529976HCID 58529976, compoundYield 11.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of benzyl 3-[4-amino-5-(2-benzyl-2H-indazol-6-yl)pyrrolo[2,1-f][1,2,4]triazin-7-yl]azetidine-1-carboxylate (304 mg, 0.57 mmol) and 6N aqueous HCl (10 mL) were stirred at 100° C. for 1 h. The mixture was concentrated to dryness. The residue was purified by preparative HPLC using a gradient elution from 15% to 50% acetonitrile in water followed by filtration through an acidic resin, washing with MeOH. The product was eluted with 2M NH3 in MeOH and the filtrate was concentrated to provide 26 mg (11%) of the desired product, which was approximately 70% pure. ES-MS m/z 396.42 [M+H]+, HPLC RT (min) 2.04.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. customThe residue was purified by preparative HPLC
  3. washa gradient elution from 15% to 50% acetonitrile in water
  4. filtrationfollowed by filtration through an acidic resin
  5. washwashing with MeOH
  6. washThe product was eluted with 2M NH3 in MeOH
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e51d48edf15f4699a16e0e25930442d7
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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