Sodium Carbonate → HCID 131736245, compound

HRID 1052634Notes

Reaction equation

HRID 1052634 reaction equation
Br[C:2]1[C:10]2[C:9]([NH:11][C@H:12]([C:14]3[N:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:18](=[O:26])[C:17]4=[C:27]([CH3:30])[CH:28]=[CH:29][N:16]4[N:15]=3)[CH3:13])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[CH:3]=1.[CH3:39][N:40]([CH3:56])[CH:41]1[CH2:46][CH2:45][N:44]([C:47]2[CH:52]=[C:51](B(O)O)[CH:50]=[CH:49][N:48]=2)[CH2:43][CH2:42]1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:39][N:40]([CH3:56])[CH:41]1[CH2:42][CH2:43][N:44]([C:47]2[CH:52]=[C:51]([C:2]3[C:10]4[C:9]([NH:11][C@H:12]([C:14]5[N:19]([C:20]6[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=6)[C:18](=[O:26])[C:17]6=[C:27]([CH3:30])[CH:28]=[CH:29][N:16]6[N:15]=5)[CH3:13])=[N:8][CH:7]=[N:6][C:5]=4[N:4]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[CH:3]=3)[CH:50]=[CH:49][N:48]=2)[CH2:45][CH2:46]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 90102148HCID 90102148, compoundHCID 131736122(S)-2-(1-((5-Bromo-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

Product 1

HCID 131736245HCID 131736245, compoundYield 104.3%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

(S)-2-(1-((5-Bromo-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, 0.08 mmol) was treated with (2-(4-(dimethylamino)piperidin-1-yl)pyridin-4-yl)boronic acid (43 mg, 0.17 mmol), tetrakis(triphenylphosphine)palladium(0) (15 mg, 0.01 mmol), aqueous solution 2M of sodium carbonate (200 μl, 0.4 mmol) and 5 ml N,N-dimethylformide as a solvent according to the method described in Preparation 186 but stirring at 100° C. overnight. The crude was purified by reverse phase using SP1® Purification System (hexane-ethyl acetate) to obtain 60 mg (75% yield) of the title compound. Purity 75%.

Workup

  1. customdescribed in Preparation 186
  2. customThe crude was purified by reverse phase
  3. custom® Purification System (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-a0cf85bdef794feaa47ff21de7e4c266
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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