Diisopropylethylamine → HCID 58928793, compound

HRID 853692Notes

Reaction equation

HRID 853692 reaction equation
FC(F)(F)C([O-])=O.[CH3:8][O:9][P:10]([CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)(=[O:13])[O:11][CH3:12].C(N(C(C)C)CC)(C)C.[CH:31]([O:44][C:45]1[C:54]2[N:53]=[CH:52][CH:51]=[CH:50][C:49]=2[C:48]([C:55](O)=[O:56])=[C:47]2[CH2:58][N:59]([CH2:62][C:63]3[CH:68]=[CH:67][C:66]([F:69])=[CH:65][CH:64]=3)[C:60](=[O:61])[C:46]=12)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[CH3:12][O:11][P:10]([CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][N:19]([C:55]([C:48]2[C:49]3[CH:50]=[CH:51][CH:52]=[N:53][C:54]=3[C:45]([O:44][CH:31]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[C:46]3[C:60](=[O:61])[N:59]([CH2:62][C:63]4[CH:64]=[CH:65][C:66]([F:69])=[CH:67][CH:68]=4)[CH2:58][C:47]=23)=[O:56])[CH2:20][CH2:21]1)(=[O:13])[O:9][CH3:8]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 84468TrifluoroacetateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58928692HCID 58928692, compoundHCID 58928996HCID 58928996, compound

Product 1

HCID 58928793HCID 58928793, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the trifluoroacetate salt of (2-piperazin-1-yl-ethyl)-phosphonic acid dimethyl ester 187 (0.023 g, 0.077 mmol) in 1 ml DMF was added diisopropylethylamine (33 μL, 0.192 mmol). This mixture was added to a solution of 9-benzhydryloxy-7-(4-fluoro-benzyl)-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinoline-5-carboxylic acid 213 (0.020 g, 0.038 mmol) that had been mixed with HATU (0.0293 g, 0.077 mmol) in 1 ml of DMF. The reaction was stirred at rt under inert atmosphere for 3 h, at which time TLC in 100% EtOAc showed complete consumption of starting material. The reaction mixture was introduced directly onto silica gel (99/1 EtOH/Et3N) to give 20 mg of (2-{4-[9-benzhydryloxy-7-(4-fluoro-benzyl)-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinoline-5-carbonyl]-piperazin-1-yl}-ethyl)-phosphonic acid dimethyl ester 291 after flash chromatography.

Workup

  1. customcomplete consumption of starting material
  2. additionThe reaction mixture was introduced directly onto silica gel (99/1 EtOH/Et3N)

Sources & evidence

ORD record
ord-4f55deda26674d57baaa54a226af3d01
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

Loading…