HCID 136343926, compound → HCID 136343927, compound

HRID 552085Notes

Reaction equation

HRID 552085 reaction equation
CO[N:3](C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:4]1[NH:5][C:6](=[O:23])[C:7]2[N:8]=[CH:9][N:10]([C@@H:13]3[O:17][C@H:16]([CH2:18][OH:19])[CH2:15][C@:14]3([C:21]#[CH:22])[F:20])[C:11]=2[N:12]=1>CC(O)=O.C1COCC1.O>[C:21]([C@:14]1([F:20])[CH2:15][C@@H:16]([CH2:18][OH:19])[O:17][C@H:13]1[N:10]1[CH:9]=[N:8][C:7]2[C:6](=[O:23])[NH:5][C:4]([NH2:3])=[N:12][C:11]1=2)#[CH:22]

Participants

3

Reactant 1

HCID 136343926HCID 136343926, compound

Product 1

HCID 136343927HCID 136343927, compound

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

15 (0.09 mmol) was stirred in AcOH/THF/H2O (3/6/1) solution at 50° C. for 1 day. The reaction mixture was then concentrated under reduced pressure and purified by silica gel chromatography, C18 (H2O/ACN) Beige lyophilisated powder. Molecular Formula C12H12FN5O5. 1H NMR (DMSO-d6, 400 MHz) δ (ppm) 2.57-2.74 (m, 2H), 3.56 (s, 1H), 3.61-3.64 (d, J=12.10 Hz, 1H), 3.79-3.82 (d, J=12.10 Hz, 1H), 3.91-3.93 (d, J=5.40 Hz, 1H), 4.32-4.35 (m, 1H), 5.25 (s, 1H), 6.06-6.10 (d, J=18.20 Hz, 1H), 6.64 (s, 1H), 8.01 (s, 1H), 10.82 (s, 1H) 19F NMR (DMSO-d6, 376 MHz) δ (ppm) −138.4 (s, 1F). Scan ES− 292 (M+H)−, Scan ES+ 316 (M+Na)+, UV λmax 251 nm

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-9f282fd2b7eb498b85078345eac2d171
Source dataset
uspto-grants-2011_05
Patent number
US07951789B2

Reaction notes

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