Hydrogen Bromide → HCID 131722982, compound

HRID 429051Notes

Reaction equation

HRID 429051 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][NH:11][C:12]2[C:13]3[C:30]4[CH:31]=[N:32][N:33]([CH2:34][CH3:35])[C:29]=4[N:28]=[CH:27][C:14]=3[C:15]([N:18]3[CH:22]=[C:21]([C:23]([NH:25][CH3:26])=[O:24])[N:20]=[CH:19]3)=[N:16][N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[BrH:36]>C(O)C>[BrH:36].[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][NH:11][C:12]2[C:13]3[C:30]4[CH:31]=[N:32][N:33]([CH2:34][CH3:35])[C:29]=4[N:28]=[CH:27][C:14]=3[C:15]([N:18]3[CH:22]=[C:21]([C:23]([NH:25][CH3:26])=[O:24])[N:20]=[CH:19]3)=[N:16][N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 9805655HCID 9805655, compound

Product 1

HCID 131722982HCID 131722982, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of the product from Example 170 (1.0 g, 2.0 mmol) in ethanol (16.6 mL) was added hydrobromic acid solution (30 wt % in acetic acid, 2.0 mL, 10.0 mmol) at 20° C. while stirring. The yellow slurry was stirred at r.t. for 3 h, and DSC analysis on a filtered wet sample showed a melt endotherm at ˜260° C. The slurry was filtered, and the filter cake was washed with 40 mL of ethanol and dried at 45° C. vacuum over for 24 h. The product was obtained as a pale yellow solid (1.1 g, 92% yield) with a HPLC purity of 99%; mp 244-248° C.; Anal. Calcd for C23H22ClN9O2.HBr: C, 48.22; H, 4.05; N, 22.01; Cl, 6.19; Br, 13.95. Found: C, 48.02; H, 3.98; N, 21.87; Cl, 6.13; Br, 13.83.

Workup

  1. stirringThe yellow slurry was stirred at r.t. for 3 h
  2. customat ˜260° C
  3. filtrationThe slurry was filtered
  4. washthe filter cake was washed with 40 mL of ethanol
  5. customdried at 45° C. vacuum over for 24 h

Sources & evidence

ORD record
ord-dfdb95e420144877a0476e98859dc41b
Source dataset
uspto-grants-2001_11
Patent number
US06316438B1

Reaction notes

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