Diisopropylethylamine → HCID 71285812, compound

HRID 246281Notes

Reaction equation

HRID 246281 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1([C:13]([OH:16])([CH3:15])[CH3:14])[CH2:12][CH2:11][CH2:10]1.C(N(CC)C(C)C)(C)C.[F:26][C:27]1[CH:35]=[C:34]2[C:30]([C:31]([C:37]3[N:38]=[C:39]4[C:45]([C:46](O)=[O:47])=[CH:44][N:43]([CH2:49][O:50][CH2:51][CH2:52][Si:53]([CH3:56])([CH3:55])[CH3:54])[C:40]4=[N:41][CH:42]=3)=[N:32][N:33]2[CH3:36])=[CH:29][CH:28]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[OH:16][C:13]([C:9]1([NH:8][C:46]([C:45]2[C:39]3[C:40](=[N:41][CH:42]=[C:37]([C:31]4[C:30]5[C:34](=[CH:35][C:27]([F:26])=[CH:28][CH:29]=5)[N:33]([CH3:36])[N:32]=4)[N:38]=3)[N:43]([CH2:49][O:50][CH2:51][CH2:52][Si:53]([CH3:56])([CH3:55])[CH3:54])[CH:44]=2)=[O:47])[CH2:12][CH2:11][CH2:10]1)([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 712796202-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acidHCID 71280181HCID 71280181, compound

Product 1

HCID 71285812HCID 71285812, compoundYield 102.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a round-bottomed flask, 2-(1-amino-cyclobutyl)-propan-2-ol trifluoroacetate (214 mg, 0.62 mmol) was dissolved in DMF (1.2 ml) and N,N-diisopropylethylamine (0.44 ml, 2.52 mmol). Then 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (110 mg, 0.25 mmol) and HATU (104 mg, 0.27 mmol) were added. The yellow reaction mixture was stirred at room temperature overnight then water and petroleum ether were added. The resulting precipitate was collected by filtration. The filter cake was washed with water and petroleum ether then dried under high vacuum to afford 142 mg (98%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [1-(1-hydroxy-1-methyl-ethyl)-cyclobutyl]-amide as an off-white powder.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washThe filter cake was washed with water and petroleum ether
  3. customthen dried under high vacuum

Sources & evidence

ORD record
ord-8baf42ac0892448cb478263393cc74ce
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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