HCID 44305612, compound → HCID 44305611, compound

HRID 1767037Notes

Reaction equation

HRID 1767037 reaction equation
[CH2:1]1[CH:3]([CH2:4][N:5]2[CH:14]3[CH2:15][C:16]4[CH:21]=[CH:20][C:19]([OH:22])=[C:18]5[O:23][C@H:9]6[C:10]7[NH:31][C:30]8[C:25](=[C:26]([N:32]=[C:33]([NH2:35])[NH2:34])[CH:27]=[CH:28][CH:29]=8)[C:11]=7[CH2:12][C@:13]3([OH:24])[C@:8]6([C:17]=45)[CH2:7][CH2:6]2)[CH2:2]1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH2:2]1[CH:3]([CH2:4][N:5]2[CH:14]3[CH2:15][C:16]4[CH:21]=[CH:20][C:19]([OH:22])=[C:18]5[O:23][C@H:9]6[C:10]7[NH:31][C:30]8[CH:25]=[C:26]([N:32]=[C:33]([NH2:35])[NH2:34])[CH:27]=[CH:28][C:29]=8[C:11]=7[CH2:12][C@:13]3([OH:24])[C@:8]6([C:17]=45)[CH2:7][CH2:6]2)[CH2:1]1

Participants

4

Reactant 1

HCID 44305612HCID 44305612, compound

Product 1

HCID 44305611HCID 44305611, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 6b (500 mg, 0.75 mmol) was dissolved in a mixture of TFA (3.0 mL) and dried CH2Cl2 (28 mL) and allowed to stir under N2 atmosphere at room temperature for 36 h. The reaction was worked up according to the procedure for compound 4a and purified by preparative TLC to give 4b (260 mg, 74%) as a free base; IR KBr disk υ (cm−1): 3450–3150 (br), 1683 (s), 1506, 1463, 1433, 1330, 1202, 1132; 1H NMR (DMSO-d6): δ 11.50 (s, 1H, NH), 9.96 (s, 11H, NH), 9.29 (s, 1H, NH), 8.95 (s, 1H, Ar—OH), 7.36–7.09 (m, 3H, ArH and NH2), 6.77 (d, 1H, J=8.10 Hz, ArH), 6.59–6.52 (m, 2H, ArH), 6.39 (s, 1H), 5.67 (s, 1H, 5-H), 4.05 (b, 1H, 14-OH), 3.43–3.23 (m, 3H), 3.18–3.06 (m, 2H), 2.96–2.91 (m, 2H), 2.68–2.57 (m, 2H), 2.50 (m, 1H), 1.78 (d, 1H, J=11.7 Hz), 1.05 (m, 1H), 0.68 (m, 1H), 0.58 (m, 1H), 0.40 (m, 2H). HRMS (FAB) m/z 472.2356 (M+H)+, C27H29N5O3 requires 471.2270.

Workup

  1. custompurified by preparative TLC

Sources & evidence

ORD record
ord-5c353a9d902c4398b75b9381519d36ea
Source dataset
uspto-grants-2007_06
Patent number
US07232829B2

Reaction notes

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