Hydrochloric Acid → HCID 24995003, compound

HRID 2392006Notes

Reaction equation

HRID 2392006 reaction equation
Cl.CC([N:6]([CH2:10][CH:11]([NH:19][C:20]([C:22]1[N:23]([CH3:33])[CH:24]=[C:25]([C:27]2[N:31]([CH3:32])[N:30]=[CH:29][CH:28]=2)[CH:26]=1)=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C(=O)[O-])(C)C>O1CCOCC1.C(Cl)(Cl)Cl.CO>[NH2:6][CH2:10][CH:11]([NH:19][C:20]([C:22]1[N:23]([CH3:33])[CH:24]=[C:25]([C:27]2[N:31]([CH3:32])[N:30]=[CH:29][CH:28]=2)[CH:26]=1)=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86633553HCID 86633553, compound

Product 1

HCID 24995003HCID 24995003, compoundYield 32.3%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 21584188Chloroform methanolSolvent

Procedure

HCl in Dioxane (4M, 2 mL) was added to a solution of 1,1-dimethylethyl[2-({[1-methyl-4-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrol-2-yl]carbonyl}amino)-3-phenylpropyl]carbamate (285 mg, 0.65 mmol) in CHCl3/MeOH (10:1, 10 mL) affording the title compound as a white solid (71 mg, 0.21 mmol, 32%): LC-MS (ES) m/z 338 (M+H)+, 1H NMR (400 MHz, MeOD) δ ppm 2.77-2.93 (m, 4H) 3.86 (s, 3H) 3.92 (s, 3H) 4.29 (ddd, J=8.15, 4.74, 2.02 Hz, 1H) 6.30 (d, J=2.02 Hz, 1H) 6.94 (d, J=1.77 Hz, 1H) 7.14 (d, J=1.77 Hz, 1H) 7.19 (td, J=5.56, 3.03 Hz, 1H) 7.25-7.30 (m, 4H) 7.41 (d, J=1.77 Hz, 1H).

Sources & evidence

ORD record
ord-48d98a7185184a3daea67330044f05a6
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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