Sodium Cyanide → HCID 68655951, compound

HRID 843132Notes

Reaction equation

HRID 843132 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[O:18][C:19]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][CH2:29][CH2:30][NH:31][CH2:32][C:33]5[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=5)[C:20]=4[C:21]=3[CH3:22])=[CH:11][C:9]=2[CH:10]=1)=O)C.[C-]#[N:40].[Na+].C(Cl)Cl.CO>N>[CH3:22][C:21]1[C:20]2[C:23]([O:27][CH2:28][CH2:29][CH2:30][NH:31][CH2:32][C:33]3[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=3)=[CH:24][CH:25]=[CH:26][C:19]=2[O:18][C:17]=1[CH2:16][O:15][C:12]1[CH:13]=[CH:14][C:8]2[O:7][C:6]([C:4]([NH2:40])=[O:3])=[CH:10][C:9]=2[CH:11]=1

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 21226129Dichloromethane methanolHCID 68655164HCID 68655164, compound

Product 1

HCID 68655951HCID 68655951, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

The compound in Example 36 (12 mg, 0.022 mmol) and NaCN (1 mg) in saturated NH3 anhydrous MeOH solution was heated at 70° C. in a sealed flask overnight. Silica gel column chromatography (CH2Cl2/MeOH=20/1 to 10/1) gave desired product (10 mg, 88%) as a colorless solid. FAB-MS: m/z 486 (MH+); 1H-NMR (CD3OD): δ 2.01 (2H, m); 2.26 (3H, s), 2.80 (1H, t, J=6.9 Hz), 3.78 (2H, s), 4.10 (1H, t, J=5.9 Hz), 5.04 (2H, s), 5.80 (1H, brs), 6.50 (1H, brs), 6.52 (1H, d, J=7.6 Hz), 7.04-7.20 (5H, m), 7.33 (1H, d, J=8.9 Hz), 7.39 (1H, s), 8.41 (1H, brd, J=4.5 Hz), 8.49 (1H, brs).

Workup

  1. customwas heated at 70° C. in a sealed flask overnight

Sources & evidence

ORD record
ord-047bc84e842a471abee543257085f925
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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