Phenyl chloroformate → HCID 57585066, compound

HRID 2077579Notes

Reaction equation

HRID 2077579 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]3[N:12]=[C:13]([NH2:15])[S:14][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[N:18]([CH3:20])[CH3:19].Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23]>N1C=CC=CC=1.C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]3[N:12]=[C:13]([NH:15][C:22](=[O:23])[O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[S:14][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[N:18]([CH3:20])[CH3:19]

Participants

6

Reactant 2

HCID 15891Phenyl chloroformateHCID 57584985HCID 57584985, compound

Product 1

HCID 57585066HCID 57585066, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 6-(6-chloro-5-(dimethylamino)pyridin-3-yl)benzo[d]thiazol-2-amine (100 mg, 328 μmol) in pyridine (0.3 mL) and DCM (2 mL) was added phenyl chloroformate (200 μl, 1594 mmol). A clear solution formed. After overnight at rt, the slurry was diluted with EtOAc (10 mL) and filtered. The solid was washed with EtOAc, then H2O (2×3 mL). LCMS indicted that the organic liquid contains most of product and by-product. The small amount of solid remained on the filter was pure product (35 mg). MS (ESI, pos. ion) m/z: calc'd for C21H17ClN4O2S: 424.1. found: 425.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.85 (s, 6H) 7.33 (t, J=7.53 Hz, 3H) 7.48 (t, J=7.78 Hz, 2H) 7.76-7.88 (m, 3H) 8.35 (s, 1H) 8.43 (s, 1H) 12.73 (s, 1H).

Workup

  1. customA clear solution formed
  2. filtrationfiltered
  3. washThe solid was washed with EtOAc

Sources & evidence

ORD record
ord-357e9ff652a541cf81651bfc3a3b8fdf
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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