Water → HCID 90102565, compound

HRID 1052829Notes

Reaction equation

HRID 1052829 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]=[CH:33][NH:34]2)=[CH:30][CH:29]=1.[H-].[Na+].[CH3:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([S:47](Cl)(=[O:49])=[O:48])=[CH:43][CH:42]=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]=[CH:33][N:34]2[S:47]([C:44]2[CH:43]=[CH:42][C:41]([O:40][CH3:39])=[CH:46][CH:45]=2)(=[O:49])=[O:48])=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 74014-Methoxybenzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 73774944HCID 73774944, compound

Product 1

HCID 90102565HCID 90102565, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

((S)-2-(1-((6-Amino-5-(1H-indol-6-yl)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (126 mg, 0.26 mmol) was added to a suspension of sodium hydride (14 mg, 0.37 mmol, 60% dispersion in mineral oil) at 0° C. After 30 min., 4-methoxybenzene-1-sulfonyl chloride was added dropwise. After 10 min. the reaction was let to warm to room temperature. After 1 h the crude was poured over a mixture of ice and water. Ethyl acetate was added and the organic phase was washed with water and brine. After evaporation of the solvent, the residue was purified by flash chromatography using SP1® Purification System (50-100% hexane/Ethyl acetate) to give 75 mg (42% yield). Purity 97%.

Workup

  1. waitAfter 10 min. the reaction was let
  2. washthe organic phase was washed with water and brine
  3. customAfter evaporation of the solvent
  4. customthe residue was purified by flash chromatography
  5. customSP1® Purification System (50-100% hexane/Ethyl acetate)
  6. customto give 75 mg (42% yield)

Sources & evidence

ORD record
ord-2b7c68ceac784d0d87fcd8dcb15c6e62
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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