Trifluoroacetic acid methylene chloride → HCID 118274195, compound

HRID 522239Notes

Reaction equation

HRID 522239 reaction equation
C([O:5][C:6](=[O:39])[CH:7]=[C:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:19][CH:18]=[C:17]([C:20]3[CH2:21][N:22]([CH3:38])[CH:23]=[C:24]4[C:33]=3[NH:32][N:31]=[C:30]3[C:26]5[C:27](=[CH:34][C:35]([F:37])=[CH:36][C:25]4=5)[CH:28]=[CH:29]3)[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)(C)(C)C.ClCCl.FC(F)(F)C(O)=O>>[F:37][C:35]1[CH:34]=[C:27]2[CH:28]=[CH:29][C:30]3=[N:31][NH:32][C:33]4[C:24](=[CH:23][N:22]([CH3:38])[CH2:21][C:20]=4[C:17]4[CH2:18][CH2:19][N:14]([CH:11]5[CH2:10][CH2:9][C:8](=[CH:7][C:6]([OH:39])=[O:5])[CH2:13][CH2:12]5)[CH2:15][CH:16]=4)[C:25](=[C:26]23)[CH:36]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 131735523HCID 131735523, compound

Product 1

HCID 118274195HCID 118274195, compound

Procedure

A mixture of Example 175B (90 mg, 0.119 mmol) in 1:1 dichloromethane/trifluoroacetic acid (0.6 mL) was stirred at room temperature for 3 hours. The reaction mixture was concentrated in vacuo to provide the title compound as bis-trifluroacetic acid salt. 1H NMR (400 MHz, Pyridine-d5) δ 1.68-2.43 (m, 8H), 2.99 (s, 3H), 3.18-3.61 (m, 4H), 4.05 (d, J=3.7 Hz, 2H), 4.32-4.47 (m, 3H), 5.93-6.15 (m, 2H), 7.15-7.32 (m, 2H), 7.44 (d, J=5.2 Hz, 1H), 7.88 (dd, J=10.4, 3.0 Hz, 1H), 8.63 (d, J=5.2 Hz, 1H), 12.82 (s, 1H). MS (ESI+) m/z 473.1 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-6e4cb3d373504315a8d0bde1f6a2a1da
Source dataset
uspto-grants-2016_05
Patent number
US09328112B2

Reaction notes

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