Acetic Acid → HCID 24937834, compound

HRID 1097979Notes

Reaction equation

HRID 1097979 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[C:10](=[O:12])[N:9]([CH:13]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]1)[CH2:8]2)#[N:2].Br.C(O)(=[O:28])C>>[O:12]=[C:10]1[C:11]2[C:3]([C:1]([NH2:2])=[O:28])=[CH:4][CH:5]=[CH:6][C:7]=2[CH2:8][N:9]1[CH:13]1[CH2:17][CH2:16][NH:15][CH2:14]1

Participants

4

Reactant 3

HCID 176Acetic Acid2×HCID 260Hydrogen BromideHCID 66812319HCID 66812319, compound

Product 1

HCID 24937834HCID 24937834, compound

Procedure

To a solution of EXAMPLE 13A (238 mg) in glacial acetic acid (2 mL) was added 33% hydrobromic acid in acetic acid (3 mL), and the mixture was stirred at ambient temperature for 2 hours and concentrated. The concentrate was purified by HPLC (Zorbax C-8, 0.1% trifluoroacetic acid/acetonitrile/water) and treated as described in EXAMPLE 7, Step B. 1H NMR (CD3OD) δ 2.34-2.44 (m, 1H), 2.45-2.56 (m, 1H), 3.37-3.47 (m, 1H), 3.57-3.66 (m, 1H), 3.67-3.78 (m, 2H), 4.66 (d, J=3.4 Hz, 2H), 4.71-4.78 (m, 1H), 7.78 (t, J=7.5 Hz, 1H), 7.87 (d, J=4.0 Hz, 1H), 7.89 (d, J=4.9 Hz, 1H).

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by HPLC (Zorbax C-8, 0.1% trifluoroacetic acid/acetonitrile/water) and
  3. additiontreated

Sources & evidence

ORD record
ord-0988a6982fc24e04851dbdf0e86b53e5
Source dataset
uspto-grants-2012_03
Patent number
US08143284B2

Reaction notes

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