Diisopropylethylamine → HCID 44540691, compound

HRID 1616003Notes

Reaction equation

HRID 1616003 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:9]([OH:11])=O)=[N:5][CH:6]=[CH:7][CH:8]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[NH:45]1[C:53]2[C:48](=[C:49]([C:54]3[CH:55]=[C:56]([NH2:63])[C:57]4[CH:58]=[N:59][NH:60][C:61]=4[CH:62]=3)[CH:50]=[CH:51][CH:52]=2)[CH:47]=[CH:46]1>CN(C=O)C>[NH:45]1[C:53]2[C:48](=[C:49]([C:54]3[CH:62]=[C:61]4[C:57]([CH:58]=[N:59][NH:60]4)=[C:56]([NH:63][C:9]([C:4]4[C:3]([O:2][CH3:1])=[CH:8][CH:7]=[CH:6][N:5]=4)=[O:11])[CH:55]=3)[CH:50]=[CH:51][CH:52]=2)[CH:47]=[CH:46]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 132095403-Methoxypyridine-2-carboxylic acidHCID 582680196-(1H-indol-4-yl)-1H-indazol-4-amine

Product 1

HCID 44540691HCID 44540691, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(Methyloxy)-2-pyridinecarboxylic acid (available from Milestone Pharm Tech, 123 mg, 0.81 mmol), O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (306 mg, 0.81 mmol) and DIPEA (0.422 ml) were stirred in DMF (2 ml) for 30 mins under nitrogen. Then 6-(1H-indol-4-yl)-1H-indazol-4-amine (100 mg, 0.40 mmol) was added and the reaction was stirred overnight. The reaction was loaded onto an aminopropyl column and left for 3 h, before eluting with 10% MeOH in DCM. Appropriate fractions were combined and evaporated under vacuum. The residue was purified by Mass Directed Automated Preparative HPLC (Method B). The solvent was dried under a stream of nitrogen to give the title compound (49 mg).

Workup

  1. waitleft for 3 h
  2. washbefore eluting with 10% MeOH in DCM
  3. customevaporated under vacuum
  4. customThe residue was purified by Mass Directed Automated Preparative HPLC (Method B)
  5. customThe solvent was dried under a stream of nitrogen

Sources & evidence

ORD record
ord-55c1444ccb034b768ecae97f8149f0cf
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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