Diisopropylethylamine → HCID 67238409, compound

HRID 880520Notes

Reaction equation

HRID 880520 reaction equation
C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[CH3:34][O:35][CH2:36][CH2:37][N:38]1[CH:42]=[CH:41][C:40]([C:43]2[CH:47]=[CH:46][S:45][CH:44]=2)=[C:39]1[C:48](=[O:52])[C:49]([OH:51])=O.[CH3:53][C:54]1[CH:59]=[C:58]([CH3:60])[N:57]=[C:56]([N:61]2[CH2:66][CH2:65][N:64]([C:67]3[CH:72]=[CH:71][C:70]([NH2:73])=[CH:69][CH:68]=3)[CH2:63][CH2:62]2)[CH:55]=1>ClCCl>[CH3:53][C:54]1[CH:59]=[C:58]([CH3:60])[N:57]=[C:56]([N:61]2[CH2:66][CH2:65][N:64]([C:67]3[CH:72]=[CH:71][C:70]([NH:73][C:49](=[O:51])[C:48]([C:39]4[N:38]([CH2:37][CH2:36][O:35][CH3:34])[CH:42]=[CH:41][C:40]=4[C:43]4[CH:47]=[CH:46][S:45][CH:44]=4)=[O:52])=[CH:69][CH:68]=3)[CH2:63][CH2:62]2)[CH:55]=1

Participants

6

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 668513514-[4-(4,6-Dimethyl-2-pyridyl)piperazin-1-yl]anilineHCID 66915138HCID 66915138, compound

Product 1

HCID 67238409HCID 67238409, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

Diisopropylethylamine (0.40 mL, 2.17 mmol), (2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate) (0.28 mg, 0.72 mmol) was added to a solution of [1-(2-methoxy-ethyl)-3-thiophen-3-yl-1H-pyrrol-2-yl]-oxo-acetic acid (200 mg, 0.72 mmol) in dry dichloromethane at room temperature and the reaction mixture stirred for 1 h. 4-[4-(4,6-Dimethyl-pyridin-2-yl)-piperazin-1-yl]-phenylamine (160 mg, 0.56 mmol) was added and the mixture was then heated in a sealed tube at 90° C. for 18 h. The reaction mixture was cooled to room temperature, washed with water and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure to give crude compound which was purified by preparative HPLC to afford N-{4-[4-(4,6-dimethyl-pyridin-2-yl)piperazin-1-yl]-phenyl}-2-[1-(2-methoxy-ethyl)-3-thiophen-3-yl-1H-pyrrol-2-yl]-2-oxo-acetamide (80 mg, 20%) as a solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customto give crude compound which
  6. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-101110772dbf45a89c5992a2b0eefdca
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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