HCID 72247367, compound → HCID 68592118, compound

HRID 2191025Notes

Reaction equation

HRID 2191025 reaction equation
C([NH:9][C:10]1[CH:15]=[CH:14][N:13]([CH:16]2[O:20][CH:19]([CH:21]=[CH:22][P:23]([OH:26])([OH:25])=[O:24])[CH:18]([O:27]C(=O)C3C=CC=CC=3)[CH:17]2[O:36][CH3:37])[C:12](=[O:38])[N:11]=1)(=O)C1C=CC=CC=1>[NH4+].[OH-]>[NH2:9][C:10]1[CH:15]=[CH:14][N:13]([CH:16]2[O:20][CH:19]([CH:21]=[CH:22][P:23](=[O:24])([OH:25])[OH:26])[CH:18]([OH:27])[CH:17]2[O:36][CH3:37])[C:12](=[O:38])[N:11]=1

Participants

3

Reactant 1

HCID 72247367HCID 72247367, compound

Product 1

HCID 68592118HCID 68592118, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

Compound 17.5 (37 mg, 95% yield) was synthesized from compound 17.4 (62 mg, 0.11 mmol) by treating 17.4 with concentrated NH4OH (10 ml) at 45° C. for 30 min. The reaction mixture was concentrated to dryness and purified by C-18 HPLC to afford compound 17.5. 1HNMR (D2O, 300 MHz) δ 7.65 (d, 1H), 6.29-6.45 (m, 1H), 5.96-6.10 (m, 3H), 5.85 (d, 1H), 4.42 (t, 1H), 4.10 (t, 1H), 3.91 (m, 1H), 3.40 (s, 3H), 31PNMR (D2O, 300 MHz): 0.90 ppm. LRMS [M−H]− C11H16N3O7P requires 332.1. Found 331.2.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. custompurified by C-18 HPLC
  3. customto afford compound 17.5

Sources & evidence

ORD record
ord-2eefc680c8fa48e39910e7e3575ff7f7
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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