Triethylamine hydrochloride → HCID 178458168, compound

HRID 2252232Notes

Reaction equation

HRID 2252232 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:22](=[CH:23][CH:24]=1)[C:10]1[NH:11][N:12]=[C:13]([C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)[C:9]=1[CH2:8]2)[CH:2]=[CH2:3].[N-:25]=[N+:26]=[N-:27].[Na+].N(CC)(CC)CC.Cl>CN(C=O)C>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:22](=[CH:23][CH:24]=1)[C:10]1[NH:11][N:12]=[C:13]([C:14]3[CH:15]=[CH:16][C:17]([C:18]4[NH:27][N:26]=[N:25][N:19]=4)=[CH:20][CH:21]=3)[C:9]=1[CH2:8]2)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochloride2×HCID 33557Sodium Azide2×HCID 69200692HCID 69200692, compound

Product 1

HCID 178458168HCID 178458168, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 62B (61.5 mg, 0.196 mmol), NaN3 (19.1 mg, 0.294 mmol), and Et3N.HCl (40.5 mg, 0.294 mmol) in DMF (2 mL) was heated at 140° C. for 4 hours. To this mixture were added more NaN3 (60.0 mg) and Et3N.HCl (120 mg). The reaction mixture was stirred overnight, cooled, and concentrated. The crude material was purified using the HPLC condition in Example 8 to give 20.0 mg (29%) of the desired product as brown solid. MS (DCI/NH3) m/z: 357.1 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 3.90 (s, 2H), 4.53-4.71 (m, 2H), 5.29 (dd, J=10.51, 1.70 Hz, 1H), 5.44 (dd, J=17.29, 2.03 Hz, 1H), 6.07 (m, 1H), 6.98 (dd, J=8.31, 2.20 Hz, 1H), 7.22 (d, J=2.03 Hz, 1H), 7.57 (d, J=8.14 Hz, 1H), 8.02 (d, J=8.14 Hz, 2H), 8.16 (d, J=8.48 Hz, 2H), 13.22 (s, brd, 1H).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customThe crude material was purified

Sources & evidence

ORD record
ord-56c07cc744924abc8c8b145af68fb158
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

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