Water → HCID 118433858, compound

HRID 1052826Notes

Reaction equation

HRID 1052826 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[C:3]=1[C:28]1[CH:36]=[C:35]2[C:31]([CH:32]=[N:33][N:34]2S(C2C=CC(OC)=CC=2)(=O)=O)=[CH:30][CH:29]=1.Cl.N1C=CC=CC=1.O>C(OCC)(=O)C>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[C:3]=1[C:28]1[CH:36]=[C:35]2[C:31]([CH:32]=[N:33][NH:34]2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10176127Pyridinium chlorideHCID 90102709HCID 90102709, compound

Product 1

HCID 118433858HCID 118433858, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

(S)-2-(1-((6-amino-5-(1-((4-methoxyphenyl)sulfonyl)-1H-indazol-6-yl)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (77 mg, 0.12 mmol) was treated with pyridine hydrochloride (2.7 g, 115 mmol) and heated at 180° C. for 2 h. Water and ethyl acetate were added and the organic phase was washed with water and brine and then concentrated. The residue was purified using SP1® Purification System (0% to 75%, hexane-ethyl acetate) to obtain 12 mg (22% yield) of the title compound as a white solid. Purity 98%.

Workup

  1. washthe organic phase was washed with water and brine
  2. concentrationconcentrated
  3. customThe residue was purified
  4. customSP1® Purification System (0% to 75%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-8e1687c23d2e4b1a8d5675a366e767fc
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

Loading…