Ammonia → HCID 135457553, compound

HRID 601152Notes

Reaction equation

HRID 601152 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([C:15]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[S:17](=[O:26])(=[O:25])[N:16]=2)=[C:11]([OH:27])[C:10]2[S:28][C:29](S(C)(=O)=O)=[N:30][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:35]>>[NH2:35][C:29]1[S:28][C:10]2[C:11]([OH:27])=[C:12]([C:15]3[NH:20][C:19]4[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=4[S:17](=[O:25])(=[O:26])[N:16]=3)[C:13](=[O:14])[N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:9]=2[N:30]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 135539122HCID 135539122, compound

Product 1

HCID 135457553HCID 135457553, compoundYield 100%

Procedure

The product of Example 146 (0.011 g, 0.02 mmol) was reacted with ammonia (0.5 M in dioxane, 1.3 mL, 0.64 mmol) in a pressure tube at 70° C. for 17 hours. The reaction was cooled and the resulting precipitate was collected by filtration and dried to give the title compound as a white solid (0.009 g, 100%). MS (ESI) m/z 452 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 5.43 (s, 2 H), 6.91 (s, 1 H), 7.07 (s, 1 H), 7.30 (m, 4 H), 7.52 (dd, J=24.27, 8.82 Hz, 2 H), 7.69 (t, J=7.54 Hz, 1 H), 7.85 (d, J=8.82 Hz, 1 H), 9.03 (br s, 1 H), 14.57 (brs, 1 H).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationthe resulting precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-fa8fa53f4294476c817686042592d050
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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