Ammonia → HCID 90102696, compound

HRID 1052832Notes

Reaction equation

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

Participants

Reactant 3

HCID 222Ammonia

HCID 6422Trifluoroacetic acid

HCID 131736243HCID 131736243, compound

Product 1

HCID 90102696HCID 90102696, compoundYield 67%

Procedure

(S)-2-(1-((5-(3-Hydroxy-5-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (50 mg, 0.07 mmol) was treated with trifluoroacetic acid (2 ml, 25 mmol) and a solution of ammonia (7N in methanol, 3 ml, 135 mmol) according to the method described in Example 27. The residue was purified using SP1® Purification System (DCM to DCM-Isopropyl alcohol 15%) to give 10 mg (67% yield) of the title compound. Purity 98%.

Workup

customThe residue was purified
customSP1® Purification System (DCM to DCM-Isopropyl alcohol 15%)

Sources & evidence

ORD record: ord-d3229d9f5e11429fb3b19c07bef19242
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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