Allylamine → HCID 67228591, compound

HRID 2375588Notes

Reaction equation

HRID 2375588 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([Br:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([OH:15])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:28]([NH2:31])[CH:29]=[CH2:30]>CN(C)C=O>[CH2:28]([NH:31][C:13]([C:3]1[N:4]=[N:5][C:6]2[C:11]([C:2]=1[NH2:1])=[CH:10][CH:9]=[CH:8][C:7]=2[Br:12])=[O:15])[CH:29]=[CH2:30]

Participants

5

Reactant 3

HCID 7853AllylamineHCID 682631,1'-CarbonyldiimidazoleHCID 67230019HCID 67230019, compound

Product 1

HCID 67228591HCID 67228591, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To an ice-cooled suspension of 4-amino-8-bromo-cinnoline-3-carboxylic acid (360 mg, 1.34 mmol) in dimethylformamide (5 mL) was added CDI (370 mg, 2.3 mmol) and the mixture was stirred at room temperature for 1 hour. Additional DMF (14 mL) was added to enable stirring. After an additional 1 hour at room temperature, the mixture was treated with allyl amine (120 uL, 91 mg, 1.60 mmol) in one portion. The reaction was stirred at room temperature for 1 hour and then concentrated. Purification on silica gel using a gradient of 20 to 80% ethyl acetate in hexanes afforded the title compound (300 mg, 73%). 1H NMR (300.132 MHz, CDCl3) δ 8.14 (dd, J=7.4, 1.0 Hz, 1H), 7.83 (dd, J=8.4, 1.0 Hz, 1H), 7.51 (dd, J=8.4, 7.5 Hz, 1H), 6.04-5.91 (m, 1H), 5.33 (dq, J=17.1, 1.6 Hz, 1H), 5.21 (dq, J=10.4, 1.4 Hz, 1H), 4.15 (ddt, J=6.2, 5.8, 1.6 Hz, 2H). MS APCI, m/z=307/309 (M+H). HPLC 1.59 min.

Workup

  1. stirringto enable stirring
  2. waitAfter an additional 1 hour at room temperature
  3. stirringThe reaction was stirred at room temperature for 1 hour
  4. concentrationconcentrated
  5. customPurification on silica gel using a gradient of 20 to 80% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-2e058f03d31d4cb0b8fd2db7f4a07b4c
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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