Ammonia → (S)-4-Hydroxy-N-(3-hydroxy-5-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl)benzenesulfonamide

HRID 1052761Notes

Reaction equation

HRID 1052761 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:45][S:46]([C:49]2[CH:54]=[CH:53][C:52]([O:55]C)=[CH:51][CH:50]=2)(=[O:48])=[O:47])[CH:5]=[C:6]([C:8]2[C:16]3[C:15]([NH:17][C@H:18]([C:20]4[N:25]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[C:24](=[O:32])[C:23]5=[C:33]([CH3:36])[CH:34]=[CH:35][N:22]5[N:21]=4)[CH3:19])=[N:14][CH:13]=[N:12][C:11]=3[N:10](COCC[Si](C)(C)C)[CH:9]=2)[CH:7]=1.B(Br)(Br)Br.N>ClCCl>[OH:55][C:52]1[CH:51]=[CH:50][C:49]([S:46]([NH:45][C:4]2[CH:5]=[C:6]([C:8]3[C:16]4[C:15]([NH:17][C@H:18]([C:20]5[N:25]([C:26]6[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=6)[C:24](=[O:32])[C:23]6=[C:33]([CH3:36])[CH:34]=[CH:35][N:22]6[N:21]=5)[CH3:19])=[N:14][CH:13]=[N:12][C:11]=4[NH:10][CH:9]=3)[CH:7]=[C:2]([OH:1])[CH:3]=2)(=[O:48])=[O:47])=[CH:54][CH:53]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 131736258HCID 131736258, compound

Product 1

HCID 90102000(S)-4-Hydroxy-N-(3-hydroxy-5-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl)benzenesulfonamideYield 11%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)—N-(3-Hydroxy-5-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl)-4-methoxybenzenesulfonamide (40 mg, 0.04 mmol) was treated with boron tribromide (1M in dichloromethane, 388 μl, 0.39 mmol) in dichloromethane (800 μl) and then with a solution of ammonia (7N in methanol, 800 μl, 5.60 mmol) according to the method described in Example 41. The residue was purified using SP1® Purification System (0% to 10% dichloromethane-2-propanol) to obtain 3 mg (11% yield, 88% purity) of the title compound.

Workup

  1. customThe residue was purified
  2. customSP1® Purification System (0% to 10% dichloromethane-2-propanol)

Sources & evidence

ORD record
ord-b748ab6e746e44cfada93671e87c5254
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

Loading…