Trifluoroacetic acid → HCID 178491301, compound

HRID 1752273Notes

Reaction equation

HRID 1752273 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][N:12]([C@@H:15]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]([NH2:23])=[NH:22])[C:16]3=[O:24])[CH2:11][CH2:10]2)=[O:8])=[CH:5][C:4]=1[CH3:27].[C:28]([OH:34])([C:30](F)(F)F)=O>C(#N)C.O>[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][N:12]([C@@H:15]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]4[NH:23][C:26]5[C:28](=[O:34])[CH:30]=[CH:6][CH:5]=[CH:4][C:3]=5[N:22]=4)[C:16]3=[O:24])[CH2:11][CH2:10]2)=[O:8])=[CH:5][C:4]=1[CH3:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89375763HCID 89375763, compound

Product 1

HCID 178491301HCID 178491301, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

The title compound (18 mg) was prepared following the general procedures of Example 28 starting with 2-{(R)-3-[4-(4-methoxy-3-methyl-benzoyl)-piperidin-1-yl]-2-oxo-pyrrolidin-1-yl}-acetamidine (405 mg, 0.85 mmol). HRMS calculated for C27H30N4O4 474.5646. found (ESI, [M+H]+). found 475.2345. 1H NMR (400 MHz, CDCl3-d) 8 ppm 1.74-2.11 (m, 4H) 2.22-2.44 (m, 5H) 2.57 (d, J=8.03 Hz, 1H) 3.09 (d, J=6.53 Hz, 3H) 3.28-3.40 (m, 1H) 3.50 (t, J=8.28 Hz, 2H) 3.62-3.83 (m, 1H) 3.89-3.97 (m, 3H) 4.82 (br. s, 2H) 6.87 (d, J=8.53 Hz, 1H) 7.00-7.11 (m, 1H) 7.26-7.36 (m, 5H) 7.38-7.47 (m, 1H) 7.72-7.86 (m, 3H) HPLC (Novapak 150×3.9 mm C18 column: mobile phase: 10-90% acetonitrile/water with 0.1% TFA, at 2 mL/min over 5 min.) retention time=2.874 min.

Sources & evidence

ORD record
ord-ad899c3461e84cae9d3efc6a692e2cfc
Source dataset
uspto-grants-2015_10
Patent number
US09163003B2

Reaction notes

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