Ammonia → HCID 118433930, compound

HRID 1052780Notes

Reaction equation

HRID 1052780 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]2[C:19]3[C:18]([NH:20][C@H:21]([C:23]4[N:28]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[C:27](=[O:35])[C:26]5=[C:36]([CH3:39])[CH:37]=[CH:38][N:25]5[N:24]=4)[CH3:22])=[N:17][CH:16]=[N:15][C:14]=3[N:13](COCC[Si](C)(C)C)[CH:12]=2)[CH:10]=1)[C:6]#[N:7].FC(F)(F)C(O)=O.N>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]2[C:19]3[C:18]([NH:20][C@H:21]([C:23]4[N:28]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[C:27](=[O:35])[C:26]5=[C:36]([CH3:39])[CH:37]=[CH:38][N:25]5[N:24]=4)[CH3:22])=[N:17][CH:16]=[N:15][C:14]=3[NH:13][CH:12]=2)[CH:10]=1)[C:6]#[N:7]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 131736195HCID 131736195, compound

Product 1

HCID 118433930HCID 118433930, compoundYield 56%

Procedure

(S)-3-Methoxy-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)benzonitrile (24 mg, 0.04 mmol) was treated with trifluoroacetic acid (480 μl, 6.23 mmol) and a solution of ammonia (7N in methanol, 480 μl, 3.36 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 11 mg (56% 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-459f099a17aa4574b8bcddcf046013a9
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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