Triethylamine → HCID 71269147, compound

HRID 1429404Notes

Reaction equation

HRID 1429404 reaction equation
[CH2:1]([CH:8]1[NH:15][CH2:14][C:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=2[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.[N:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][C:35]=2[S:37](Cl)(=[O:39])=[O:38])[CH:30]=[CH:29][CH:28]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:1]([CH:8]1[N:15]([S:37]([C:35]2[CH:34]=[CH:33][CH:32]=[C:31]3[C:36]=2[N:27]=[CH:28][CH:29]=[CH:30]3)(=[O:38])=[O:39])[CH2:14][C:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=2[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 292208-Quinolinesulfonyl chlorideHCID 71269598HCID 71269598, compound

Product 1

HCID 71269147HCID 71269147, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 301 (crude 1.58 mmol), Et3N (0.33 mL, 2.4 mmol) and DMAP (39 mg, 0.32 mmol) in DCM (25 mL), quinoline-8-sulfonyl chloride (538 mg, 2.37 mmol) in DCM (5 mL) was added dropwise at 0° C. After addition was complete, the solution was left to stir at rt overnight. The mixture was washed with water (2×30 mL) and brine. The organic layer was combined, dried over Na2SO4, concentrated in vacuo. MeOH (10 mL) was added to the residue and the precipitation was filtered to give the desired product (60 mg, 81% over three steps). 1H NMR (500 MHz, CDCl3) δ: 9.07 (m, 1H), 8.51 (d, 1H), 8.13 (d, 1H), 7.93 (d, 1H), 7.57 (t, 1H), 7.44 (m, 1H), 7.29 (d, 1H), 7.12 (m, 2H), 6.98 (m, 1H), 6.90 (m, 3H), 6.59 (d, 2H), 5.76 (d, 1H), 5.53 (d, 1H), 4.34 (m, 1H), 3.61 (m, 1H), 2.59 (m, 1H), 2.27 (t, 1H), 2.07 (m, 1H), 1.88 (m, 1H), 1.60 (m, 1H), 1.34 (m, 1H), 1.24 (m, 1H). MS (ESI+) m/z: 443 [M+H]+.

Workup

  1. additionAfter addition
  2. waitthe solution was left
  3. washThe mixture was washed with water (2×30 mL) and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. additionMeOH (10 mL) was added to the residue
  7. customthe precipitation
  8. filtrationwas filtered

Sources & evidence

ORD record
ord-4c0ddffbe9b444989d2d4d88909bae59
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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