Diisopropylcarbodiimide → HCID 59177922, compound

HRID 1661113Notes

Reaction equation

HRID 1661113 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[N:10]([C:33]([C@@H:36]([OH:38])[CH3:37])=[N:34][N:35]=3)[N:11]([CH2:21][C:22]3[C:23]([CH3:32])=[N:24][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:27]=3)[C:12](=[O:20])[C:13]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.[C:39]([NH:46][C@H:47]([C:51](O)=[O:52])[CH:48]([CH3:50])[CH3:49])([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40].CC(C)N=C=NC(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:42]([O:41][C:39]([NH:46][C@@H:47]([CH:48]([CH3:50])[CH3:49])[C:51]([O:38][C@H:36]([C:33]1[N:10]2[N:11]([CH2:21][C:22]3[C:23]([CH3:32])=[N:24][C:25]([C:28]([F:30])([F:29])[F:31])=[CH:26][CH:27]=3)[C:12](=[O:20])[C:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[C:9]2=[N:35][N:34]=1)[CH3:37])=[O:52])=[O:40])([CH3:45])([CH3:44])[CH3:43]

Participants

6

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 83693Boc-L-ValineHCID 59177918HCID 59177918, compound

Product 1

HCID 59177922HCID 59177922, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask was added (S)-8-(4-chlorophenyl)-3-(1-hydroxyethyl)-5-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-7-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-6(5H)-one (35 mg, 0.0648 mmol), Boc-L-Valine (15.5 mg, 0.0713 mmol), CH2Cl2(3 ml), DMAP (cat, 3 mg) and DIC (12.3 mg, 0.0973 mmol). The reaction was stirred at rt for 30 min. After this time, the solution was concentrated. The crude product was purified by silica gel column chromatography (8 g silica gel) eluting with a gradient of 0-50% EtOAc/Hex to give product (S)—((S)-1-(8-(4-chlorophenyl)-5-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-6-oxo-7-phenyl-5,6-dihydro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)ethyl) 2-(tert-butoxycarbonylamino)-3-methylbutanoate, as a white solid (39 mg, 81% yield).

Workup

  1. concentrationAfter this time, the solution was concentrated
  2. customThe crude product was purified by silica gel column chromatography (8 g silica gel)
  3. washeluting with a gradient of 0-50% EtOAc/Hex

Sources & evidence

ORD record
ord-794ea11d457b43db8fd42bde79ae9a1a
Source dataset
uspto-grants-2011_10
Patent number
US08030306B2

Reaction notes

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