Dichloromethane → HCID 178488252, compound

HRID 416303Notes

Reaction equation

HRID 416303 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:17]=[C:16]([NH:18][CH2:19][C:20]3[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=3)[NH:15][N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C(Cl)Cl.O=S(Cl)[Cl:34].[C:36]1([NH2:43])[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[NH2:42]>C1COCC1>[NH2:42][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[NH:43][C:24](=[O:25])[C:23]1[CH:27]=[CH:28][C:20]([CH2:19][NH:18][C:16]2[NH:15][N:14]=[C:13]([C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=3)[C:17]=2[Cl:34])=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7243O-PhenylenediamineHCID 24386Thionyl ChlorideHCID 178487547HCID 178487547, compound

Product 1

HCID 178488252HCID 178488252, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 389 (30 mg, 0.08 mmol) in a 1:1 mixture of DCM and SOCl2 (2 mL) was stirred at room temperature for 30 min. The reaction mixture was concentrated and treated with a solution of 1,2-phenylene diamine (18 mg, 0.16 mmol) in THF (2 mL) and stirred at room temperature for 15 min, concentrated under reduced pressure to produce a solid which was purified by preparative HPLC (column AQUASIL C-18; 5 μM; 230×21.2 mm; eluent 30-95% MeOH in water) to afford the title compound (8 mg, 20% yield). 1H NMR (MeOH-d4) 7.92 (d, J=8.3 Hz, 2H), 7.52 (d, J=8.2 Hz, 2H), 7.17 (d, J=7.6 Hz, 1H), 7.06 (m, 3H), 6.89 (d, J=7.8 Hz, 1H), 6.75 (t, J=7.2 Hz, 1H), 4.55 (s, 2H), 3.89 (s, 6H), 3.80 (s, 3H). LRMS: (calc) 507.2; (found) 508.3 (M+H1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. stirringstirred at room temperature for 15 min
  3. concentrationconcentrated under reduced pressure
  4. customto produce a solid which
  5. customwas purified by preparative HPLC (column AQUASIL C-18; 5 μM; 230×21.2 mm; eluent 30-95% MeOH in water)

Sources & evidence

ORD record
ord-eac6c31fb3dd40b0bb1b8f47b8b7ca7a
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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