Diisopropylethylamine → Phenylmethyl 3-hydroxy-4-({[6-(1H-indol-4-yl)-1H-indazol-4-yl]amino}carbonyl)-1-pyrrolidinecarboxylate

HRID 42258Notes

Reaction equation

HRID 42258 reaction equation
[OH:1][CH:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:4][CH:3]1[C:17]([OH:19])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:44]1[C:52]2[C:47](=[C:48]([C:53]3[CH:54]=[C:55]([NH2:62])[C:56]4[CH:57]=[N:58][NH:59][C:60]=4[CH:61]=3)[CH:49]=[CH:50][CH:51]=2)[CH:46]=[CH:45]1.CCN(C(C)C)C(C)C>CN(C=O)C>[OH:1][CH:2]1[CH:3]([C:17]([NH:62][C:55]2[CH:54]=[C:53]([C:48]3[CH:49]=[CH:50][CH:51]=[C:52]4[C:47]=3[CH:46]=[CH:45][NH:44]4)[CH:61]=[C:60]3[C:56]=2[CH:57]=[N:58][NH:59]3)=[O:19])[CH2:4][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[CH2:6]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 448909181-N-Cbz-4-hydroxy-beta-prolineHCID 582680196-(1H-indol-4-yl)-1H-indazol-4-amine

Product 1

HCID 44540587Phenylmethyl 3-hydroxy-4-({[6-(1H-indol-4-yl)-1H-indazol-4-yl]amino}carbonyl)-1-pyrrolidinecarboxylateYield 6.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxy-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrrolidinecarboxylic acid (available from Fluorochem, 59 mg, 0.22 mmol) in DMF (1 ml) was added HATU (85 mg, 0.22 mmol) and the mixture stirred for 10 mins. Then 6-(1H-indol-4-yl)-1H-indazol-4-amine (46 mg, 0.19 mmol) and DIPEA (0.065 ml, 0.37 mmol) were added and the mixture allowed to stand for 18 h at 20° C. The solvent was removed under a stream of nitrogen and the residue purified by Mass Directed Automated Preparative HPLC (Method E), to give the title compound (6 mg) as a brown solid.

Workup

  1. waitto stand for 18 h at 20° C
  2. customThe solvent was removed under a stream of nitrogen
  3. customthe residue purified by Mass Directed Automated Preparative HPLC (Method E)

Sources & evidence

ORD record
ord-c870562fc785452990d4e33df5171831
Source dataset
uspto-grants-2013_09
Patent number
US08536169B2

Reaction notes

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