HCID 86672489, compound → HCID 86672488, compound

HRID 1896225Notes

Reaction equation

[CH3:1][NH:2][C:3]([C@@:5]12[CH2:10][C@@H:9]1[C@@H:8]([N:11]1[CH:19]=[N:18][C:17]3[C:12]1=[N:13][C:14]([Cl:36])=[N:15][C:16]=3[NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]#[C:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]#[CH:35])[CH:23]=1)[C@H:7]([OH:37])[C@@H:6]2[OH:38])=[O:4].CNC([C@@]12C[C@@H]1[C@@H](N1C=NC3C1=NC(Cl)=NC=3NCC1C=CC=C(C#CCCCC3[N:72]=[N:73][N:74]([C:76]4[CH:81]=[CH:80][C:79]([F:82])=[C:78]([N+:83]([O-:85])=[O:84])[CH:77]=4)C=3)C=1)[C@H](O)[C@@H]2O)=O>>[CH3:1][NH:2][C:3]([C@@:5]12[CH2:10][C@@H:9]1[C@@H:8]([N:11]1[CH:19]=[N:18][C:17]3[C:12]1=[N:13][C:14]([Cl:36])=[N:15][C:16]=3[NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]#[C:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]3[N:72]=[N:73][N:74]([C:76]4[CH:81]=[CH:80][C:79]([F:82])=[C:78]([N+:83]([O-:85])=[O:84])[CH:77]=4)[CH:35]=3)[CH:23]=1)[C@H:7]([OH:37])[C@@H:6]2[OH:38])=[O:4]

Participants

Reactant 2

HCID 86672489HCID 86672489, compound

HCID 86672490HCID 86672490, compound

Product 1

HCID 86672488HCID 86672488, compoundYield 94%

Procedure

Compound 204 (94%) was synthesized from compound 201 following the same procedure as for compound 203. 1H NMR (CD3OD, 400 MHz) δ 8.65-8.58 (m, 1H), 8.45 (s, 1H), 8.23-8.19 (m, 1H), 8.03 (s, 1H), 7.65 (t, J=8.8 Hz, 1H), 7.41 (s, 1H), 7.33-7.25 (m, 2H), 5.07 (d, J=6.8 Hz, 1H), 4.80 (s, 1H), 4.72 (br s, 2H), 4.00 (d, J=6.8 Hz, 1H), 2.87 (s, 3H), 2.51 (t, J=6.8 Hz, 2H), 2.07-2.04 (m, 1H), 1.97-1.91 (m, 2H), 1.82 (t, J=5.2 Hz, 2H), 1.74-1.69 (m, 2H), 1.39-1.35 (m, 1H). HRMS calculated for C34H33ClFN10O5 (M+H)+: 715.2308. Found 715.2302.

Sources & evidence

ORD record: ord-452dd056aefc496f8421512f14a3d002
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518957B2

Reaction notes

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