Ammonia → (S)-4-Hydroxy-N-(3-(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 1052748Notes

Reaction equation

HRID 1052748 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[C:27]4[C:26]([NH:28][C@H:29]([C:31]5[N:36]([C:37]6[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=6)[C:35](=[O:43])[C:34]6=[C:44]([CH3:47])[CH:45]=[CH:46][N:33]6[N:32]=5)[CH3:30])=[N:25][CH:24]=[N:23][C:22]=4[N:21](COCC[Si](C)(C)C)[CH:20]=3)[CH:14]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.B(Br)(Br)Br.N>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[C:27]4[C:26]([NH:28][C@H:29]([C:31]5[N:36]([C:37]6[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=6)[C:35](=[O:43])[C:34]6=[C:44]([CH3:47])[CH:45]=[CH:46][N:33]6[N:32]=5)[CH3:30])=[N:25][CH:24]=[N:23][C:22]=4[NH:21][CH:20]=3)[CH:14]=2)(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 131736186(S)-4-Methoxy-N-(3-(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)benzenesulfonamide

Product 1

HCID 90102152(S)-4-Hydroxy-N-(3-(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 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-4-Methoxy-N-(3-(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)benzenesulfonamide (57 mg, 0.05 mmol) was treated with boron tribromide (1M in dichloromethane, 536 μL, 0.54 mmol) in dichloromethane (1.15 mL) and then with a solution of ammonia (7N in methanol, 1.15 ml, 6.05 mmol) according to the method described in Example 27. The residue was purified using SP1 ® Purification System (0% to 6% dichloromethane-2-propanol) to obtain 25 mg (72% yield) of the title compound.

Workup

  1. customThe residue was purified
  2. customSP1 ® Purification System (0% to 6% dichloromethane-2-propanol)

Sources & evidence

ORD record
ord-c7b7980a1c8a442298af412c2d6f3129
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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