Phosphorus oxychloride → HCID 178490050, compound

HRID 710544Notes

Reaction equation

HRID 710544 reaction equation
Cl.[NH2:2][CH2:3][C:4](=O)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:8]=1[O:15][CH3:16].[N:18]1[C:22]2[CH:23]=[CH:24][C:25]([C:27](O)=O)=[CH:26][C:21]=2[NH:20][CH:19]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:39])=CC=1.O=P(Cl)(Cl)Cl>>[NH:18]1[C:22]2[CH:23]=[CH:24][C:25]([C:27]3[S:39][C:4]([CH2:5][CH2:6][C:7]4[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:8]=4[O:15][CH3:16])=[CH:3][N:2]=3)=[CH:26][C:21]=2[N:20]=[CH:19]1

Participants

5

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 87949Lawesson's reagentHCID 4594565-Benzimidazolecarboxylic acidHCID 67393300HCID 67393300, compound

Product 1

HCID 178490050HCID 178490050, compound

Procedure

The compound was synthesized starting from amino-4-(2,3-dimethoxyphenyl)butan-2-on-hydrochloride (223 mg; 1 mmol), benzimidazol-5-carboxylic acid (248 mg; 1 mmol), Lawesson's reagent (606 mg; 1.5 mmol), TEA (0.22 ml, 3 mmol) and POCl3 (0.137 ml; 1.5 mmol) as described above; yield: 0.019 g (5.2%); MS m/z: 366.2 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): δ 2.94 (t, 2H, 3J=7.5 Hz); 3.14 (t, 2H, 3J=7.5 Hz); 3.72 (s, 3H); 3.78 (s, 3H); 6.81-6.83 (m, 1H); 6.89-6.91 (m, 1H); 6.96-7.00 (m, 1H); 7.62 (s, 1H); 7.79 (d, 1H, 3J=8.7 Hz); 7.90 (dd, 1H, 4J=1.7 Hz, 3J=8.7 Hz); 8.16 (br s, 1H); 8.97 (s, 1H); HPLC (METHOD [A]): rt 13.59 min (97.7%)

Workup

  1. customThe compound was synthesized
  2. customrt 13.59 min (97.7%)

Sources & evidence

ORD record
ord-2508de90f0bb47ca9ca2ed6a15d3d639
Source dataset
uspto-grants-2015_11
Patent number
US09181233B2

Reaction notes

Loading…