Dansyl chloride → HCID 86615486, compound

HRID 2358622Notes

Reaction equation

HRID 2358622 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[C:4]([NH:16][C:17]2[C:26]3[C:21](=[N:22][C:23]([CH3:27])=[CH:24][CH:25]=3)[N:20]=[CH:19][CH:18]=2)[CH:3]=1.[CH3:28][N:29]([CH3:44])[C:30]1[CH:39]=[CH:38][CH:37]=[C:36]2[C:31]=1[CH:32]=[CH:33][CH:34]=[C:35]2[S:40](Cl)(=[O:42])=[O:41].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][S:40]([C:35]3[C:36]4[C:31](=[C:30]([N:29]([CH3:44])[CH3:28])[CH:39]=[CH:38][CH:37]=4)[CH:32]=[CH:33][CH:34]=3)(=[O:42])=[O:41])=[CH:13][CH:14]=2)=[C:4]([NH:16][C:17]2[C:26]3[C:21](=[N:22][C:23]([CH3:27])=[CH:24][CH:25]=3)[N:20]=[CH:19][CH:18]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 11801Dansyl chlorideHCID 81531DiisopropylethylamineHCID 24897972HCID 24897972, compound

Product 1

HCID 86615486HCID 86615486, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Example 5 (167 mg, 0.94 mmol) was reacted with 5-Dimethylamino-naphthalene-1-sulfonyl chloride (245 mg, 0.94 mmol) in 10 mL of CH2Cl2 with N,N-diisopropylethylamine (0.530 mL, 410 mmol) for 22 h. Washed with water and dried over Na2SO4, filtered and concentrated under vacuum giving the crude title compound which was purified by HPLC with TFA providing the trifluoroacetic acid salt (35 mg, 40%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.75 (s, 3H) 2.86 (s, 6H) 6.65 (d, J=6.99 Hz, 1H) 6.76 (d, J=9.19 Hz, 2H) 6.87 (d, 2H) 7.16 (d, J=8.82 Hz, 1H) 7.34 (d, J=7.72 Hz, 1H) 7.53-7.62 (m, 2H) 7.69-7.79 (m, 3H) 7.97 (d, J=7.35 Hz, 1H) 8.22 (d, J=8.82 Hz, 1H) 8.50 (d, J=6.99 Hz, 1H) 8.60 (d, J=8.46 Hz, 1H) 8.82 (d, J=8.82 Hz, 1H); MS 1H) 8.50 (d, J=6.99 Hz, 1H) 8.60 (d, J=8.46 Hz, 1H) 8.82 (d, J=8.82 Hz, 1H); MS (DCI NH3+) m/z 611 (M+H)+.

Workup

  1. washWashed with water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b7a13d72621b4fe88621b130efc4c52f
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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