Diisopropylethylamine → HCID 86651928, compound

HRID 1685132Notes

Reaction equation

HRID 1685132 reaction equation
[CH3:1][O:2][C:3]1[CH:35]=[CH:34][C:6]([CH2:7][O:8][C:9]2[C:10]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:25]=[N:26][C:27]([C:30](=[O:33])[NH:31][CH3:32])=[CH:28][CH:29]=4)=[CH:20][CH:19]=3)=[N:11][N:12]([CH3:17])[C:13]=2[C:14]([OH:16])=O)=[CH:5][CH:4]=1.[CH3:36][O:37][C:38]1[CH:66]=[C:65]([O:67][CH3:68])[CH:64]=[CH:63][C:39]=1[CH2:40][NH:41][C:42]1[CH:43]=[C:44]2[C:48](=[CH:49][C:50]=1[NH2:51])[CH2:47][N:46]([CH2:52][C:53]1[CH:58]=[CH:57][C:56]([O:59][CH3:60])=[CH:55][C:54]=1[O:61][CH3:62])[CH2:45]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C>[CH3:62][O:61][C:54]1[CH:55]=[C:56]([O:59][CH3:60])[CH:57]=[CH:58][C:53]=1[CH2:52][N:46]1[CH2:47][C:48]2[C:44](=[CH:43][C:42]([NH:41][CH2:40][C:39]3[CH:63]=[CH:64][C:65]([O:67][CH3:68])=[CH:66][C:38]=3[O:37][CH3:36])=[C:50]([NH:51][C:14]([C:13]3[N:12]([CH3:17])[N:11]=[C:10]([C:18]4[CH:19]=[CH:20][C:21]([C:24]5[CH:29]=[CH:28][C:27]([C:30]([NH:31][CH3:32])=[O:33])=[N:26][CH:25]=5)=[CH:22][CH:23]=4)[C:9]=3[O:8][CH2:7][C:6]3[CH:34]=[CH:35][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[O:16])[CH:49]=2)[CH2:45]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 68052599HCID 68052599, compoundHCID 68052643HCID 68052643, compound

Product 1

HCID 86651928HCID 86651928, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(4-methoxybenzyloxy)-1-methyl-3-(4-(6-(methylcarbamoyl)pyridin-3-yl)phenyl)-1H-pyrazole-5-carboxylic acid T-13 (304 mg, 0.64 mmol) in N,N-dimethylformamide (4 mL) were added N5,2-bis(2,4-dimethoxybenzyl)isoindoline-5,6-diamine T-04 (347 mg, 0.77 mmol), HATU (318 mg, 0.84 mmol) and diisopropylethylamine (0.34 mL, 2.0 mmol). The reaction mixture was stirred at room temperature for 2 hours. The crude product was diluted with ethyl acetate. The organic layer was washed with water and saturated brine. The organic layer was dried over sodium sulfate. Solvent was evaporated under reduced pressure. The crude product was purified by flash chromatography to afford the desired 5-(4-(5-(2-(2,4-dimethoxybenzyl)-6-(2,4-dimethoxybenzylamino)isoindolin-5-ylcarbamoyl)-4-(4-methoxybenzyloxy)-1-methyl-1H-pyrazol-3-yl)phenyl)-N-methylpicolinamide T-14 (410 mg, 0.45 mmol).

Workup

  1. washThe organic layer was washed with water and saturated brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customSolvent was evaporated under reduced pressure
  4. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-2b5f49e88b4f48e0adbcc40789c83c07
Source dataset
uspto-grants-2012_04
Patent number
US08148363B2

Reaction notes

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