HCID 67317254, compound → HCID 54684192, compound

HRID 1012990Notes

Reaction equation

HRID 1012990 reaction equation
[CH3:1][N:2]([C:4](=[O:41])[C:5]([N:7]([CH3:40])[CH:8]1[CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11][N:10]2[C:22](=[O:39])[C:23]([OH:38])=[C:24]([C:26]([NH:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[C:32]([CH3:37])[CH:31]=3)=[O:27])[N:25]=[C:9]12)=[O:6])[CH3:3]>ClCCl.FC(F)(F)C(O)=O>[F:36][C:33]1[CH:34]=[CH:35][C:30]([CH2:29][NH:28][C:26]([C:24]2[N:25]=[C:9]3[CH:8]([N:7]([CH3:40])[C:5](=[O:6])[C:4]([N:2]([CH3:1])[CH3:3])=[O:41])[CH2:14][NH:13][CH2:12][CH2:11][N:10]3[C:22](=[O:39])[C:23]=2[OH:38])=[O:27])=[CH:31][C:32]=1[CH3:37]

Participants

3

Reactant 1

HCID 67317254HCID 67317254, compound

Product 1

HCID 54684192HCID 54684192, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

The compound of Step 6 was stirred in dichloromethane/trifluoroacetic acid (8/2 v/v) for 1 hour, then concentrated under reduced pressure and purified by RP HPLC (C18, 5 μM, H2O/MeCN with 1% of TFA as eluant) affording desired compound as trifluoroacetic salt. 1H NMR (300 MHz, CD3CN) δ 12.68 (bs, 1H), 9.96 (bs, 1H), 7.50 (d, J=7.51 Hz, 1H), 7.45-7.41 (m, 1H), 7.21 (t, J=8.62 Hz, 1H), 5.55-5.46 (m, 2H), 4.75 (dd, J=14.6 Hz, J=6.8 Hz, 1H), 4.67 (dd, J=14.6 Hz, J=6.3 Hz, 1H), 4.24-4.05 (m, 3H), 3.96-3.92 (m, 1H), 3.39-3.36 (m, 1H), 3.24 (s, 3H), 3.19 (s, 3H), 3.18 (s, 3H), 2.46 (s, 3H); MS (ES) C22H27FN6O5 requires 474. Found: 475 (M+H+).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by RP HPLC (C18, 5 μM, H2O/MeCN with 1% of TFA as eluant)

Sources & evidence

ORD record
ord-6ecbe283ab424241bb2fb22827f9dc5f
Source dataset
uspto-grants-2011_07
Patent number
US07981879B2

Reaction notes

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