Hydrogen Bromide → HCID 86694432, compound

HRID 1428253Notes

Reaction equation

HRID 1428253 reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([N:10]2[CH:18]3[CH:13]([N:14](C(OCC4C=CC=CC=4)=O)[CH2:15][CH2:16][CH2:17]3)[CH2:12][CH2:11]2)=[N:3][CH:2]=1.[BrH:29]>C(O)(=O)C>[BrH:29].[N:10]1([C:4]2[C:5]3[CH:9]=[CH:8][NH:7][C:6]=3[N:1]=[CH:2][N:3]=2)[CH:18]2[CH:13]([NH:14][CH2:15][CH2:16][CH2:17]2)[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 56967632HCID 56967632, compound

Product 1

HCID 86694432HCID 86694432, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of the racemic product of Example 1 (1.77 g, 4.69 mmol) in 33% HBr in acetic acid (30 mL) was stirred at ambient temperature for 2 hours. The reaction mixture was concentrated to a crude solid/liquid mixture. Ethanol (35 mL) was added, and the resulting suspension was stirred at ambient temperature. The solids were filtered, rinsing the filter cake with ethanol. The filtered solids were dried on the high vacuum until constant weight was achieved to afford the desired product (HBr salt) as a grey solid. LRMS calc'd for C13H18N5[M+H]+, 244; found 244. 1H NMR (500 MHz, DMSO-D6) δ 12.7 (br s, 1H), 9.21 (br s, 2H), 8.35 (s, 1H), 7.47 (s, 1H), 6.85 (s, 1H), 4.56 (br s, 1H), 4.30-3.76 (br m, 4H), 3.20-3.02 (br m, 2H), 2.60 (br pentet, 1H), 2.33-2.24 (br m, 1H), 2.22-2.14 (br m, 1H), 1.82-1.74 (br m, 1H), 1,74-1.52 (br m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated to a crude solid/liquid mixture
  2. additionEthanol (35 mL) was added
  3. stirringthe resulting suspension was stirred at ambient temperature
  4. filtrationThe solids were filtered
  5. washrinsing the filter cake with ethanol
  6. customThe filtered solids were dried on the high vacuum until constant weight

Sources & evidence

ORD record
ord-a01593e1cec64a32bce15663240ab433
Source dataset
uspto-grants-2015_01
Patent number
US08937077B2

Reaction notes

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