Diisopropylethylamine → HCID 178521832, compound

HRID 1037997Notes

Reaction equation

HRID 1037997 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[CH2:11][N:12]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:22].[O:23]=[C:24]([N:34]1[CH2:39][CH2:38][N:37]([C:40]2[CH:45]=[CH:44][C:43]([C:46]3[N:51]=[CH:50][CH:49]=[CH:48][N:47]=3)=[CH:42][CH:41]=2)[CH2:36][CH2:35]1)[CH2:25][N:26]1[CH2:30][CH2:29][CH:28]([C:31](O)=[O:32])[CH2:27]1.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=O)C.[Cl-].[Na+].O>[O:21]=[C:20]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[O:22])[N:12]1[CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:31]([CH:28]3[CH2:29][CH2:30][N:26]([CH2:25][C:24](=[O:23])[N:34]4[CH2:35][CH2:36][N:37]([C:40]5[CH:45]=[CH:44][C:43]([C:46]6[N:47]=[CH:48][CH:49]=[CH:50][N:51]=6)=[CH:42][CH:41]=5)[CH2:38][CH2:39]4)[CH2:27]3)=[O:32])[CH:3]=2)[NH:7][N:6]=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 674194121-{2-Oxo-2-[4-(4-pyrimidin-2-yl-phenyl)-piperazin-1-yl]-ethyl}-pyrrolidine-3-carboxylic acidHCID 178507361HCID 178507361, compound2×

Product 1

HCID 178521832HCID 178521832, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-(5-Amino-1H-indazol-3-ylmethyl)-isoindole-1,3-dione (compound 49 from Step 3, 614 gm, 2 mmol) and compound 12 (from Example 1 Step 9) were dissolved in 10 ml of DMF. O-(7-azabenzotriazol-1-yl-)-N,N,N,N-tetramethyluronium hexafluorophosphate (HATU) (660 mg, 1.7 mmol) and diisopropylethylamine (0.9 ml, 5 eq.). After stirring 4 hours, the reaction mixture was added to brine and extracted with ethylacetate, dried over magnesium sulfate and evaporated. The crude was chromatographed on silica gel to obtain 440 mg of title product.

Workup

  1. extractionextracted with ethylacetate
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customThe crude was chromatographed on silica gel

Sources & evidence

ORD record
ord-57f7a3d3131d456193b4544201e82c88
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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