Diisopropylethylamine → HCID 71288384, compound

HRID 246278Notes

Reaction equation

HRID 246278 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:13]=[C:14]4[C:20]([C:21](O)=[O:22])=[CH:19][N:18]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.Cl.[F:33][C:34]([F:46])([F:45])[O:35][C:36]1[CH:37]=[C:38]([C@@H:42]([NH2:44])[CH3:43])[CH:39]=[CH:40][CH:41]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O.CN(C=O)C>[F:33][C:34]([F:45])([F:46])[O:35][C:36]1[CH:37]=[C:38]([C@@H:42]([NH:44][C:21]([C:20]2[C:14]3[C:15](=[N:16][CH:17]=[C:12]([C:6]4[C:5]5[C:9](=[CH:10][C:2]([F:1])=[CH:3][CH:4]=5)[N:8]([CH3:11])[N:7]=4)[N:13]=3)[N:18]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:29])([CH3:31])[CH3:30])[CH:19]=2)=[O:22])[CH3:43])[CH:39]=[CH:40][CH:41]=1

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 71280121(S)-1-(3-(trifluoromethoxy)phenyl)ethanamine hydrochloride

Product 1

HCID 71288384HCID 71288384, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A 10 ml round-bottomed flask was charged with 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (100 mg, 0.23 mmol) and (S)-1-(3-trifluoromethoxy-phenyl)-ethylamine hydrochloride (155 mg, 0.45 mmol). DMF (1.1 ml) was added followed by N,N-diisopropylethylamine (0.28 ml, 1.6 mmol) and HATU (95 mg, 0.25 mmol). The yellow reaction mixture was stirred at room temperature overnight then water and petroleum ether were added. The resulting off-white precipitate was collected by filtration. The filter cake was washed with water and petroleum ether then dried under high vacuum to afford 126 mg (89%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(S)-1-(3-trifluoromethoxy-phenyl)-ethyl]-amide as an off-white powder.

Workup

  1. filtrationThe resulting off-white 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-9df402916aa345e2bf67498ca0662c00
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

Loading…