Dimethylcarbamoyl Chloride → HCID 73690419, compound

HRID 2121932Notes

Reaction equation

HRID 2121932 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[C:14]2[N:18]([CH3:19])[C:17]3[CH:20]=[C:21]([OH:24])[CH:22]=[CH:23][C:16]=3[S:15]2)[S:10][C:9]1=[N:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[NH:34][CH2:35][CH3:36])[C:29]#[N:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:37][N:38]([CH3:42])[C:39](Cl)=[O:40]>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[C:14]2[N:18]([CH3:19])[C:17]3[CH:20]=[C:21]([O:24][C:39](=[O:40])[N:38]([CH3:42])[CH3:37])[CH:22]=[CH:23][C:16]=3[S:15]2)[S:10][C:9]1=[N:25][C:26]1[CH:27]=[C:28]([C:29]#[N:30])[CH:31]=[CH:32][C:33]=1[NH:34][CH2:35][CH3:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 73855097HCID 73855097, compound

Product 1

HCID 73690419HCID 73690419, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of the product of Example 57 in CHCl3 was added TEA (84 μL, 0.6 mmol) and dimethylcarbamoyl chloride (56 μL, 0.6 mmol). The resulted suspension was heated to 65° C. overnight with shaking. Solvent was removed under vacuum to give a crude, which was purified by chromatography on silica gel, eluting by MeOH-DCM (5:95) to afford the title compound (38.6 mg). 1H-NMR indicated one isomer. 1H-NMR (DMSO-d6): δ 97.73 (1H, d), 7.28-7.39 (7H, m), 7.14 (1H, d), 6.97 (1H, dd), 6.63 (1H, dd), 5.12 (2H, s), 4.98 (1H, t), 3.78 (3H, s), 3.05 (6H, m), 2.91 (3H, s), 0.99 (3H, t); MS (ESI): 585 (MH+).

Workup

  1. customSolvent was removed under vacuum
  2. customto give a crude, which
  3. customwas purified by chromatography on silica gel
  4. washeluting by MeOH-DCM (5:95)

Sources & evidence

ORD record
ord-95a874024b0749fcbc1ba5be43e40868
Source dataset
uspto-grants-2004_02
Patent number
US06696473B2

Reaction notes

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