HCID 178442423, compound → HCID 178442424, compound

HRID 1881493Notes

Reaction equation

HRID 1881493 reaction equation
[CH3:1][C:2]([CH3:37])([CH2:35][CH3:36])[CH2:3][C:4]1[N:5]=[C:6]([C:9]2([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][N:29]=4)=[CH:24][CH:23]=3)[CH2:13][CH2:12][CH2:11][N:10]2C(OC(C)(C)C)=O)[NH:7][CH:8]=1>FC(F)(F)C(O)=O>[CH3:1][C:2]([CH3:37])([CH2:35][CH3:36])[CH2:3][C:4]1[N:5]=[C:6]([C:9]2([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][N:29]=4)=[CH:24][CH:23]=3)[CH2:13][CH2:12][CH2:11][NH:10]2)[NH:7][CH:8]=1

Participants

3

Reactant 1

HCID 178442423HCID 178442423, compound

Product 1

HCID 178442424HCID 178442424, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 2-[4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]-2-[4-(5-fluoropyridin-2-yl)benzyl]pyrrolidine-1-carboxylate (45 mg, 0.089 mmol) was dissolved in trifluoroacetic acid (1 mL). After stirring at ambient temperature overnight, the reaction mixture was concentrated in vacuo to afford the title compound. 1H NMR (500 MHz, CD3OD) δ 8.48 (d, J=2.5 Hz, 1H), 8.28 (br s, 1H), 7.83 (dd, J=8.7, 4.2 Hz, 1H), 7.79 (d, J=8.0 Hz, 2H), 7.64 (td, J=8.5, 3.0 Hz, 1H), 6.97 (d, J=8.0 Hz, 2H), 6.86 (s, 1H), 3.45-3.39 (m, 3H), 3.24-3.17 (m, 1H), 2.52-2.41 (m, 1H), 2.45 (s, 2H), 2.33-2.25 (m, 1H), 2.22-2.13 (m, 1H), 1.91-1.82 (m, 1H), 1.22 (q, J=15.0, 7.5 Hz, 2H), 0.84 (t, J=7.5 Hz, 3H), 0.81 (s, 6H). (M+H) found: 407.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-54f91ad7beb24140bae8eec3356ea7f0
Source dataset
uspto-grants-2012_11
Patent number
US08318767B2

Reaction notes

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