Hydrochloric Acid → HCID 69742620, compound

HRID 458429Notes

Reaction equation

HRID 458429 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:31]2[O:32][CH:33]=[C:34]([C:36]([OH:38])=O)[N:35]=2)=[C:8]2[C:26](=[O:27])[N:25]3[CH2:28][CH2:29][CH2:30][N:24]3[C:9]2=[N:10][C:11]=1[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1)=[O:5])[CH3:2].CCN=C=[N:43][CH2:44][CH2:45][CH2:46]N(C)C.[CH:50]1[CH:51]=[CH:52][C:53]2N(O)N=N[C:54]=2[CH:55]=1.Cl>C(Cl)Cl>[C@H:44]1([NH:43][C:36]([C:34]2[N:35]=[C:31]([C:7]3[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:11]([CH2:12][CH2:13][C:14]4[CH:15]=[CH:16][C:17]([C:20]([F:22])([F:21])[F:23])=[CH:18][CH:19]=4)[N:10]=[C:9]4[N:24]5[CH2:30][CH2:29][CH2:28][N:25]5[C:26](=[O:27])[C:8]=34)[O:32][CH:33]=2)=[O:38])[C:54]2[C:53](=[CH:52][CH:51]=[CH:50][CH:55]=2)[CH2:46][CH2:45]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 18441893HCID 18441893, compound

Product 1

HCID 69742620HCID 69742620, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(3-(ethoxycarbonyl)-5-oxo-2-{2-[4-(trifluoromethyl)phenyl]ethyl}-8,9-dihydro-5H,7H-pyrazolo[1′,2′:1,2]pyrazolo[3,4-b]pyridin-4-yl)-1,3-oxazole-4-carboxylic acid (0.076 g, 0.143 mmol) was dissolved in CH2Cl2 (2 mL). R-(−)-1-aminoindane (0.018 mL, 0.215 mmol) was added followed by EDCI (0.033 g, 0.172 mmol) and HOBt (0.023 g, 0.172 mmol). After 14 h of stirring at ambient temperature the reaction mixture was poured onto 5% HCl solution and extracted with CH2Cl2. The organics were washed with sat'd NaHCO3, brine and then dried (Na2SO4), filtered and concentrated to a yellow residue. Chromatography on silica gel using 9:1 EtOAc:Hexanes eluted the product to provide the title compound upon concentration as a white solid (0.046 g, 0.0.071 mmol, 50% yield): 1H NMR (CDCl3, 400 MHz) 8.44 (s, 1H), 7.49 (d, J=7.9 Hz, 2H), 7.29–7.12 (m, 6H), 5.64 (dd, J=15.7, 7.6 Hz, 1H), 4.58 (d J=5.9 Hz, 2H), 4.07 (dd, J=14.3, 7.0 Hz, 2H), 3.99–3.91 (m, 4H), 3.24–3.10 (m, 4H), 3.04–2.97 (m, 1H), 2.92–2.84 (m, 1H), 1.93–1.87 (m, 1H), 1.04 (t, J=7.1 Hz, 3H); ESMS m/z 646 (M+H)+, 644 (M−H)+ Anal. Calcd. For C34H30F3N5O5.½H2O: C, 62.38; H, 4.77; N, 10.70; found: C, 62.59; H, 4.74; N, 10.58.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organics were washed with sat'd NaHCO3, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to a yellow residue
  6. washChromatography on silica gel using 9:1 EtOAc:Hexanes eluted the product

Sources & evidence

ORD record
ord-0ab53b6ffb244434b8558daa2b924bfd
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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