Ammonia → HCID 118433787, compound

HRID 1052781Notes

Reaction equation

HRID 1052781 reaction equation
C[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].B(Br)(Br)Br.N>ClCCl>[OH: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

5

Reactant 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 131736195HCID 131736195, compound

Product 1

HCID 118433787HCID 118433787, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 (34 mg, 0.05 mmol) was treated with boron tribromide (1M in dichloromethane, 526 μL, 0.53 mmol) in dichloromethane (680 μL) and then with a solution of ammonia (7N in methanol, 680 μl, 4.76 mmol) according to the method described in Example 41. The residue was purified using SP1® Purification System (0% to 15% dichloromethane-2-propanol) to obtain 19 mg (69% 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-fadb465e8603495d9ac911f4cceccd3f
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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