HCID 68230499, compound → HCID 53472543, compound

HRID 1631447Notes

Reaction equation

HRID 1631447 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:17]([NH:19][CH2:20][CH2:21][CH2:22][NH:23]C(OC(C)(C)C)=O)=[O:18])[CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)[N:6]2[N:5]=[CH:4][N:3]=1.N1(C(OCC(C)(C)C(N[C@H]2CC[C@H](N)CC2)=O)=O)CCOCC1>CO.O>[NH2:1][C:2]1[C:7]2=[C:8]([C:17]([NH:19][CH2:20][CH2:21][CH2:22][NH2:23])=[O:18])[CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 68230499HCID 68230499, compoundHCID 178452429HCID 178452429, compound

Product 1

HCID 53472543HCID 53472543, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

20 was prepared from 19 (40 mg, 0.097 mmol) by the general method shown for 15D. 20.2TFA (10 mg, 19% yield) was obtained as a sticky, off-white solid. HPLC: 0.83 min (YMC S5 ODS, 4.5×50 mm. 4 mL/min, 10-90% methanol-water 0.2% H3PO4, gradient over 12 min). MS (ES): m/z=312 [M+H]+. 1H NMR (400 MHz, DMSO-d6+MeOH-d4) δ ppm 8.81 (d, 2H, J=6.8 Hz); 8.41 (d, 2H, J=6.5 Hz); 8.18 (s, 1H); 8.09 (s, 1H); 3.39 (t, 2H, J=6.5 Hz); 2.87 (t, 2H, J=7.7 Hz); 1.80-1.89 (m, 2H).

Workup

  1. custom20.2TFA (10 mg, 19% yield) was obtained as a sticky, off-white solid

Sources & evidence

ORD record
ord-532ebf331abc48988bb6b724cbcc5dc4
Source dataset
uspto-grants-2014_07
Patent number
US08791257B2

Reaction notes

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