(Diethylamino)sulfur trifluoride → HCID 75202655, compound

HRID 925425Notes

Reaction equation

HRID 925425 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:13]=[C:12]([CH3:14])[N:11]=[C:10]([C:15]3(O)[CH2:18][CH:17]([C:19]4[N:23]([CH3:24])[C:22]5[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=5[N:20]=4)[CH2:16]3)[CH:9]=2)[N:3]=1.CCN(S(F)(F)[F:36])CC>C(Cl)Cl>[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:13]=[C:12]([CH3:14])[N:11]=[C:10]([C:15]3([F:36])[CH2:18][CH:17]([C:19]4[N:23]([CH3:24])[C:22]5[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=5[N:20]=4)[CH2:16]3)[CH:9]=2)[N:3]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 75202521HCID 75202521, compound

Product 1

HCID 75202655HCID 75202655, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 1 (20 mg, 0.051 mmol) in dry CH2Cl2 (2 mL) was added DAST (16 mg, 0.102 mmol) at −78° C. The solution was allowed to warm to room temperature over 1 h at which time LCMS indicated the reaction was complete. The reaction mixture was concentrated and the crude residue was purified by reverse-phase chromatography (5-30% MeOH/H2O) to give Example 2 as a white solid. 1H NMR (400 MHz, CD3OD) δ 7.96-7.86 (m, 3H), 7.74-7.60 (m, 2H), 4.69-4.52 (m, 1H), 4.05 (s, 3H), 3.51-3.34 (m, 4H), 2.91 (s, 3H), 2.55 (s, 3H), 2.41 (s, 3H). MS: m/z=392.2 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe crude residue was purified by reverse-phase chromatography (5-30% MeOH/H2O)

Sources & evidence

ORD record
ord-103ce17b5c7e49b19bf606fc2ebd011e
Source dataset
uspto-grants-2016_03
Patent number
US09284302B2

Reaction notes

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