Methanol → HCID 118433836, compound

HRID 1052823Notes

Reaction equation

HRID 1052823 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:16]=[C:15]3[C:11]([CH:12]=[CH:13][N:14]3COCC[Si](C)(C)C)=[C:10]([NH:25][S:26]([C:29]3[CH:34]=[CH:33][C:32]([O:35]C)=[CH:31][CH:30]=3)(=[O:28])=[O:27])[CH:9]=2)=[C:6]([NH:37][C@H:38]([C:40]2[N:45]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:44](=[O:52])[C:43]3=[C:53]([CH3:56])[CH:54]=[CH:55][N:42]3[N:41]=2)[CH3:39])[N:5]=[CH:4][N:3]=1.B(Br)(Br)Br.CO>ClCCl>[NH2:1][C:2]1[C:7]([C:8]2[CH:16]=[C:15]3[C:11]([CH:12]=[CH:13][NH:14]3)=[C:10]([NH:25][S:26]([C:29]3[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=3)(=[O:28])=[O:27])[CH:9]=2)=[C:6]([NH:37][C@H:38]([C:40]2[N:45]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:44](=[O:52])[C:43]3=[C:53]([CH3:56])[CH:54]=[CH:55][N:42]3[N:41]=2)[CH3:39])[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 131736191HCID 131736191, compound

Product 1

HCID 118433836HCID 118433836, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)—N-(6-(4-Amino-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidin-5-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indol-4-yl)-4-methoxybenzenesulfonamide (56 mg, 0.07 mmol) was dissolved in dichloromethane (1 ml). A solution of boron tribromide (1M in dichloromethane, 707 μl, 0.71 mmol) was added dropwise and the reaction was stirred at room temperature overnight. Methanol was added and the solvents were removed. Then ammonia (7N in methanol) (1.5 ml) was added and the mixture was stirred at room temperature overnight. The solvent was removed and the residue was purified by reverse phase chromatography using SP1® Purification System to give 6 mg (20% yield) of the title compound as a white solid. Purity 97%.

Workup

  1. customthe solvents were removed
  2. additionThen ammonia (7N in methanol) (1.5 ml) was added
  3. stirringthe mixture was stirred at room temperature overnight
  4. customThe solvent was removed
  5. customthe residue was purified by reverse phase chromatography
  6. customSP1® Purification System

Sources & evidence

ORD record
ord-3c3036cc8f9d46d093922ad9d18d389e
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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