Ammonia → HCID 118433889, compound

HRID 1052862Notes

Reaction equation

HRID 1052862 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:45][S:46]([CH2:49][CH2:50][O:51]C)(=[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>[F:1][C:2]1[CH:3]=[C:4]([NH:45][S:46]([CH2:49][CH2:50][OH:51])(=[O:47])=[O:48])[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:27]=[CH:28][CH:29]=[CH:30][CH:31]=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[NH:10][CH:9]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 131736206(S)-N-(3-Fluoro-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)-2-methoxyethanesulfonamide

Product 1

HCID 118433889HCID 118433889, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)—N-(3-Fluoro-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)-2-methoxyethanesulfonamide (29 mg, 0.03 mmol, 78% purity) was treated with boron tribromide (1M in dichloromethane, 303 μl, 0.30 mmol) with dichloromethane (580 μl) as a solvent according to the method described in Example 23. and then with a solution of ammonia (7N in methanol, 600 μl, 4.20 mmol) according to the method described in Example 27. The residue was purified using SP1® Purification System (0% to 15% dichloromethane-2-propanol) to obtain 15 mg (82% yield) of the title compound.

Workup

  1. customThe residue was purified
  2. customSP1® Purification System (0% to 15% dichloromethane-2-propanol)

Sources & evidence

ORD record
ord-67c21459dc0948bb919376d7527c6530
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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