Carbon Dioxide → HCID 58204102, compound

HRID 708137Notes

Reaction equation

HRID 708137 reaction equation
C(OC(=O)[NH:7][C:8]([CH3:40])([CH3:39])[CH2:9][N:10]1[CH:14]=[C:13]([C:15]2[CH:38]=[CH:37][C:18]3[C:19]4[N:20]=[C:21]([C:27]5[N:28]([CH2:32][C:33]([F:36])([F:35])[F:34])[N:29]=[CH:30][N:31]=5)[S:22][C:23]=4[CH2:24][CH2:25][O:26][C:17]=3[CH:16]=2)[CH:12]=[N:11]1)(C)(C)C.C(Cl)Cl.FC(F)(F)C(O)=O.C(=O)=O>>[CH3:40][C:8]([NH2:7])([CH3:39])[CH2:9][N:10]1[CH:14]=[C:13]([C:15]2[CH:38]=[CH:37][C:18]3[C:19]4[N:20]=[C:21]([C:27]5[N:28]([CH2:32][C:33]([F:36])([F:35])[F:34])[N:29]=[CH:30][N:31]=5)[S:22][C:23]=4[CH2:24][CH2:25][O:26][C:17]=3[CH:16]=2)[CH:12]=[N:11]1

Participants

5

Reactant 4

HCID 280Carbon DioxideHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 58203945HCID 58203945, compound

Product 1

HCID 58204102HCID 58204102, compoundYield 15%

Procedure

To a round bottom flask containing [1,1-Dimethyl-2-(4-{2-[2-(2,2,2-trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl}-pyrazol-1-yl)-ethyl]-carbamic acid tert-butyl ester (0.175 g, 0.000297 mol) in methylene chloride (1.1 mL, 0.017 mol) was added trifluoroacetic acid (1.3 mL, 0.017 mol). The solution was stirred at room temperature until CO2 evolution stopped (30 minutes). The solvent was removed in vacuo and purified by reverse-phase HPLC to give 393 (21.8 mg) as a white solid. MS(ESI+) 490.1. 1H NMR (400 MHz, DMSO) δ 8.37 (d, J=9.7, 1H), 8.29 (s, 1H), 8.26 (d, J=8.3, 1H), 7.98 (s, 1H), 7.49 (dd, J=8.3, 1.7, 1H), 7.37 (d, J=1.7, 1H), 5.86 (q, J=8.7, 2H), 4.39 (t, J=5.0, 2H), 3.47 (t, J=5.0, 2H), 2.86 (s, 2H), 1.50 (s, 6H).

Workup

  1. custom(30 minutes)
  2. customThe solvent was removed in vacuo
  3. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-f5948d15260e4444b65a66ad25fbec57
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

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