Dimethylformamide → HCID 86609537, compound

HRID 1865482Notes

Reaction equation

HRID 1865482 reaction equation
[CH:1]1([CH2:4][S:5]([CH:8]2[CH2:13][CH2:12][C:11]([CH2:18][NH:19][C:20]([C:22]3[C:23]([CH3:33])=[N:24][C:25](S(C)(=O)=O)=[N:26][C:27]=3C)=[O:21])([CH2:14][CH:15]3[CH2:17][CH2:16]3)[CH2:10][CH2:9]2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.[C-:34]#N.[Na+].[CH3:37][N:38](C=O)C>>[CH:1]1([CH2:4][S:5]([CH:8]2[CH2:9][CH2:10][C:11]([CH2:18][NH:19][C:20]([C:22]3[CH:27]=[N:26][C:25]([C:37]#[N:38])([CH3:34])[NH:24][C:23]=3[CH3:33])=[O:21])([CH2:14][CH:15]3[CH2:17][CH2:16]3)[CH2:12][CH2:13]2)(=[O:7])=[O:6])[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 86609538HCID 86609538, compound

Product 1

HCID 86609537HCID 86609537, compound

Procedure

To a stirred solution of 2-methanesulfonyl-4,6-dimethyl-pyrimidine-5-carboxylic acid (4-cyclopropylmethanesulfonyl-1-cyclopropylmethyl-cyclohexylmethyl)-amide (82 mg; 0.165 mmol) in DMF (2 ml) was added sodium cyanide (12 mg; 0.247 mmol) and the mixture was stirred at room temperature for 90 minutes. The mixture was evaporated in vacuo, coevaporating with toluene, to give an orange oil. The oil was partitioned between EtOAc (20 ml) and water (20 ml). The organic phase was separated, washed with water (20 ml) and brine (20 ml), dried (MgSO4) and evaporated in vacuo to give a yellow oil. The crude product was purified by prep. TLC eluted with 50% EtOAc in hexane to give the product as a white foam (43 mg). 1H NMR (400 MHz, CDCl3): δ 5.96 (1H, t, J 6.2), 3.64 (2H, d, J 6.4), 2.99-2.93 (1H, m), 2.87 (2H, d, J 7.1), 2.57 (6H, s), 2.04-1.84 (6H, m), 1.47-1.39 (2H, m), 1.27-1.23 (2H, m), 1.16-1.08 (1H, m), 0.79-0.67 (3H, m), 0.55-0.51 (2H, m), 0.42-0.38 (2H, m), 0.05-0.03 (2H, m). m/z=445 (M+H+).

Workup

  1. customThe mixture was evaporated in vacuo
  2. customto give an orange oil
  3. customThe oil was partitioned between EtOAc (20 ml) and water (20 ml)
  4. customThe organic phase was separated
  5. washwashed with water (20 ml) and brine (20 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. customto give a yellow oil
  9. customThe crude product was purified by prep
  10. washTLC eluted with 50% EtOAc in hexane

Sources & evidence

ORD record
ord-dea2bd1c48e743bcb1294b1624e0931a
Source dataset
uspto-grants-2009_12
Patent number
US07626056B2

Reaction notes

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