1,2-Dichloroethane → HCID 86687393, compound

HRID 1473344Notes

Reaction equation

HRID 1473344 reaction equation
[NH:1]1[CH2:4][CH:3]([N:5]2[C:9]([C:10]3[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:11]=3[C:20]3[CH:29]=[CH:28][CH:27]=[C:26]4[C:21]=3[CH:22]=[CH:23][C:24]([S:30]([NH:33][C:34]3[S:35][CH:36]=[CH:37][N:38]=3)(=[O:32])=[O:31])=[CH:25]4)=[CH:8][CH:7]=[N:6]2)[CH2:2]1.Cl[CH2:40]CCl.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CC(O)=O>[CH3:40][N:1]1[CH2:2][CH:3]([N:5]2[C:9]([C:10]3[CH:15]=[C:14]([C:16]([F:19])([F:17])[F:18])[CH:13]=[CH:12][C:11]=3[C:20]3[CH:29]=[CH:28][CH:27]=[C:26]4[C:21]=3[CH:22]=[CH:23][C:24]([S:30]([NH:33][C:34]3[S:35][CH:36]=[CH:37][N:38]=3)(=[O:31])=[O:32])=[CH:25]4)=[CH:8][CH:7]=[N:6]2)[CH2:4]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86687394HCID 86687394, compound

Product 1

HCID 86687393HCID 86687393, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A flask was charged with 5-(2-(1-(azetidin-3-yl)-1H-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide (26.25 mg, 0.047 mmol), DCE (1 mL), AcOH (0.05 mL), and formaldehyde (37% aq.) (10.55 μl, 0.142 mmol). The mixture was stirred for 2 min, then sodium triacetoxyborohydride (20.03 mg, 0.094 mmol) was added in one portion. The resulting mixture was stirred for 3 h, then concentrated. The residue was dissolve in MeOH, and this solution was loaded onto a 500 mg SCX-2 ion exchange column (Biotage AB, Uppsala, SE). The column was eluted with methanol, then with 2N ammonia in methanol. The basic fraction was concentrated to afford 5-(2-(1-(1-methylazetidin-3-yl)-1H-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide (23.53 mg, 0.041 mmol) as a beige-solid. 1H NMR (400 MHz, DMSO-d6) δ ppm=8.40 (s, 1H), 8.09 (d, J=7.9 Hz, 1H), 8.00 (d, J=6.9 Hz, 1H), 7.82 (s, 1H), 7.74 (d, J=8.4 Hz, 2H), 7.62-7.51 (m, 2H), 7.39 (d, J=6.8 Hz, 1H), 7.29 (s, 1H), 7.15 (d, J=4.1 Hz, 1H), 6.71 (d, J=4.0 Hz, 1H), 5.99 (s, 1H), 4.59 (td, J=7.3, 14.2 Hz, 1H), 3.66-3.59 (m, 1H), 3.33 (t, J=7.0 Hz, 1H), 3.09-2.95 (m, 2H), 2.27 (s, 3H). m/z (ESI) 570.2 (M+H)+.

Workup

  1. stirringThe resulting mixture was stirred for 3 h
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolve in MeOH
  4. washThe column was eluted with methanol
  5. concentrationThe basic fraction was concentrated

Sources & evidence

ORD record
ord-af9da096b16f46ffa106972217ed644f
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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