Diisopropylethylamine → HCID 58413175, compound

HRID 240618Notes

Reaction equation

HRID 240618 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][CH2:35][C@H:34]([O:38][C:39]2[CH:44]=[C:43]([F:45])[CH:42]=[CH:41][C:40]=2[NH:46][C:47]2[C:48]3[C:55]([CH3:56])=[C:54]([C:57](O)=[O:58])[S:53][C:49]=3[N:50]=[CH:51][N:52]=2)[CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].CCN(C(C)C)C(C)C.[CH3:69][N:70]1[CH:74]=[CH:73][C:72]([NH2:75])=[N:71]1>CN(C=O)C>[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][CH2:35][C@H:34]([O:38][C:39]2[CH:44]=[C:43]([F:45])[CH:42]=[CH:41][C:40]=2[NH:46][C:47]2[C:48]3[C:55]([CH3:56])=[C:54]([C:57](=[O:58])[NH:75][C:72]4[CH:73]=[CH:74][N:70]([CH3:69])[N:71]=4)[S:53][C:49]=3[N:50]=[CH:51][N:52]=2)[CH2:33]1)=[O:31])([CH3:27])([CH3:28])[CH3:26]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1372541-Methyl-3-aminopyrazoleHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58413177HCID 58413177, compound

Product 1

HCID 58413175HCID 58413175, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU was added into a solution of 4-[2-((S)-1-tert-Butoxycarbonyl-piperidin-3-yloxy)-4-fluoro-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid (100 mg) and DIPEA in anhydrous DMF (2 ml) at 0° C. The reaction was stirred for 0.5 h when 1-methyl-1H-pyrazol-3-amine (100 μl) was added and the reaction allowed to warm to room temperature and stirred for 2 h. The DMF was removed by co-evaporation from toluene and the residue was purified by chromatography to give the intended product.

Workup

  1. additionwas added
  2. customThe DMF was removed by co-evaporation from toluene
  3. customthe residue was purified by chromatography
  4. customto give the intended product

Sources & evidence

ORD record
ord-2c7c1bb3e3c1478dbd62017dc4d3bc39
Source dataset
uspto-grants-2014_02
Patent number
US08648068B2

Reaction notes

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