Dansyl chloride → HCID 86615486, compound

HRID 883890Notes

Reaction equation

HRID 883890 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 19 (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, 3 H) 2.86 (s, 6 H) 6.65 (d, J=6.99 Hz, 1 H) 6.76 (d, J=9.19 Hz, 2 H) 6.87 (d, 2 H) 7.16 (d, J=8.82 Hz, 1 H) 7.34 (d, J=7.72 Hz, 1 H) 7.53-7.62 (m, 2 H) 7.69-7.79 (m, 3 H) 7.97 (d, J=7.35 Hz, 1 H) 8.22 (d, J=8.82 Hz, 1 H) 8.50 (d, J=6.99 Hz, 1 H) 8.60 (d, J=8.46 Hz, 1 H) 8.82 (d, J=8.82 Hz, 1 H); MS 1 H) 8.50 (d, J=6.99 Hz, 1 H) 8.60 (d, J=8.46 Hz, 1 H) 8.82 (d, J=8.82 Hz, 1 H); 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-e57eeb13cc6443d9b32ea8c90f2c69d1
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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