Water → HCID 58529400, compound

HRID 1972797Notes

Reaction equation

HRID 1972797 reaction equation
[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([C:33](C)(C)[O:34][SiH2]C(C)(C)C)[CH:28]=4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.O>CCO.Cl>[NH2:26][C:24]1[C:25]2=[C:17]([C:12]3[CH:13]=[CH:14][C:15]4[C:10]([CH:11]=3)=[N:9][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:16]=4)[CH:18]=[C:19]([C:27]3[CH:28]=[C:29]([CH2:33][OH:34])[CH:30]=[CH:31][CH:32]=3)[N:20]2[N:21]=[CH:22][N:23]=1

Participants

6

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 131730545HCID 131730545, compound

Product 1

HCID 58529400HCID 58529400, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

The product from step 4 (367 mg, 0.65 mmol) was dissolved in 4 mL of 1:1 EtOH:THF and 0.5 mL of water was added followed by the addition of 1 drop of concentrated aqueous HCl. The mixture was stirred for 1 hour (ppt formed) and the solid was collected by filtration, washed with THF and air dried overnight to give 286 mg (98%) of the title compound as a white solid. 1H-NMR (DMSO-d6) 9.00 (bs, 1H), 8.63 (s, 1H), 8.26 (s, 1H), 8.02, (s, 1H) 7.96-7.86 (m, 2H) 7.80 (s, 1H), 7.49 (t, 1H), 7.46-7.30 (m, 6H), 7.28 (d, 1H), 7.26 (bs, 1H), 5.72 (s, 2H), 4.60 (s, 2H); LC-MS [M+H]+=447.3, RT=2.72 min.

Workup

  1. custom(ppt formed)
  2. filtrationthe solid was collected by filtration
  3. washwashed with THF and air
  4. customdried overnight

Sources & evidence

ORD record
ord-ceff44f0a33643849f6dbfad7db4db57
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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