Dimethylformamide → HCID 73855062, compound

HRID 2121933Notes

Reaction equation

HRID 2121933 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.[C:37]([O-:40])([O-])=O.[K+].[K+].[CH3:43]N(C=O)C>>[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][CH2:43][CH2:37][OH:40])[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

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 73855097HCID 73855097, compound

Product 1

HCID 73855062HCID 73855062, compound

Conditions

Temperature
75 °C

Procedure

To a solution of the product of Example 57 in DMF were added K2CO3 and 3-bromoethanol and the resulting suspension was heated to 75° C. with stirring under nitrogen for 72 h. Solid was removed by filtration and washed by DMF. Evaporation of solvent gave a crude, which was purified by chromatography on silica gel eluting with MeOH-DCM (5:95) to afford the title compound (0.58 g). 1H-NMR indicated one isomer. 1H-NMR (DMSO-d6): δ 7.62 (1H, d), 7.29-7.39 (5H, m), 7.14 (1H, d), 7.02 (1H, d), 6.84 (1H, dd), 5.75 (1H, d), 5.11 (2H, s), 4.97 (1H, t), 4.87 (1H, t), 4.05 (2H, t), 3.80 (3H, s, 3.71 (2H, m), 3.05 (2H, m), 0.99 (3H, t); MS (ESI): 558 (MH+).

Workup

  1. customSolid was removed by filtration
  2. washwashed by DMF
  3. customEvaporation of solvent
  4. customgave a crude, which
  5. customwas purified by chromatography on silica gel eluting with MeOH-DCM (5:95)

Sources & evidence

ORD record
ord-a319f98a65d84ea096556cbe05f6be9b
Source dataset
uspto-grants-2004_02
Patent number
US06696473B2

Reaction notes

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