Triethylamine → (S)-N-(3-Methoxy-5-(3-(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)-1H-pyrazol-1-yl)phenyl)methanesulfonamide

HRID 1052646Notes

Reaction equation

HRID 1052646 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:10]2[CH:14]=[CH:13][C:12]([C:15]3[C:23]4[C:22]([NH:24][C@H:25]([C:27]5[N:32]([C:33]6[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=6)[C:31](=[O:39])[C:30]6=[C:40]([CH3:43])[CH:41]=[CH:42][N:29]6[N:28]=5)[CH3:26])=[N:21][CH:20]=[N:19][C:18]=4[N:17]([CH2:44][O:45][CH2:46][CH2:47][Si:48]([CH3:51])([CH3:50])[CH3:49])[CH:16]=3)=[N:11]2)[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.C(N(CC)CC)C.[CH3:59][S:60](Cl)(=[O:62])=[O:61]>N1C=CC=CC=1>[CH3:9][O:8][C:6]1[CH:7]=[C:2]([NH:1][S:60]([CH3:59])(=[O:62])=[O:61])[CH:3]=[C:4]([N:10]2[CH:14]=[CH:13][C:12]([C:15]3[C:23]4[C:22]([NH:24][C@H:25]([C:27]5[N:32]([C:33]6[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=6)[C:31](=[O:39])[C:30]6=[C:40]([CH3:43])[CH:41]=[CH:42][N:29]6[N:28]=5)[CH3:26])=[N:21][CH:20]=[N:19][C:18]=4[N:17]([CH2:44][O:45][CH2:46][CH2:47][Si:48]([CH3:51])([CH3:49])[CH3:50])[CH:16]=3)=[N:11]2)[CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 131736246(S)-2-(1-((5-(1-(3-Amino-5-methoxyphenyl)-1H-pyrazol-3-yl)-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 131736247(S)-N-(3-Methoxy-5-(3-(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)-1H-pyrazol-1-yl)phenyl)methanesulfonamideYield 94%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

(S)-2-(1-((5-(1-(3-Amino-5-methoxyphenyl)-1H-pyrazol-3-yl)-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 (15.3 mg, 0.02 mol) was dissolved in 2 ml pyridine and triethylamine (5 μl, 0.04 mol). The mixture was submitted to three vacuum-argon cycles and was cooled at 0° C. with an ice bath. Methanesulfonyl chloride (2 μl, 0.03 mol) was added dropwise and the reaction mixture was stirred for 2 h. The solvent was concentrated and the residue was partitioned between ethyl acetate and a saturated sodium bicarbonate solution. The organic phase was dried over sodium sulphate and evaporated under reduced pressure, to obtain 16.6 mg (94% yield) of the title compound. Purity 72%.

Workup

  1. concentrationThe solvent was concentrated
  2. customthe residue was partitioned between ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1255e9f1c42e46c3a3eb28aad4b4c2e9
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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