Acetonitrile → HCID 86749354, compound

HRID 1440809Notes

Reaction equation

HRID 1440809 reaction equation
[OH:1][C@H:2]1[C@H:11]([N:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:21])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:22]3[C:23](=O)[C:24](=[O:30])[C:25]=3[O:26]C(C)C)[CH:9]=2)[O:4][C:3]1([CH3:33])[CH3:32].CC#[N:36]>>[NH2:36][C:23]1[C:24](=[O:30])[C:25](=[O:26])[C:22]=1[C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[O:4][C:3]([CH3:32])([CH3:33])[C@@H:2]([OH:1])[C@@H:11]2[N:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:21]

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 86749353HCID 86749353, compound

Product 1

HCID 86749354HCID 86749354, compound

Procedure

To a solution of 154 mg (0.344 mmol) of 3-[trans-3-hydroxy-2,2-dimethyl-4-(1-oxo-1,3-dihydroisoindol-2-yl)-chroman-6-yl]-4-isopropoxy-cyclobut-3-ene-1,2-dione as prepared in Example 3 in CH3CN was bubbled ammonia gas for 30 min. The reaction mixture was then sealed and stirred for 16 h. The reaction mixture was concentrated. Flash chromatography (CH2Cl2 : MeOH: NH4OH (94.75/3.5/1.75)) followed by crystallization from THF and petroleum ether gave 136 mg of the title compound as a white solid, mp>250° C.: 1H-NMR (DMSO-d6 ; 400 MHz) δ8.90 (br s, 1 H), 8.76 (br s, 1 H), 7.7-7.8 (m, 3 H), 7.51-7.63 (m, 3 H), 6.98 (d, 1 H), 1.48 (s, 3 H), and 1.27 ppm (s, 3 H); IR (KBr) 1780, 1730, 1670, and 1640 cm-1 ; mass spectrum (+CI), m/e 405. Anal. Calcd. for C23H20N2OS: C, 68.31; H, 4.98; N, 6.93 Found.: C, 67.91; H, 5.12; N, 6.78.

Workup

  1. customwas bubbled ammonia gas for 30 min
  2. customThe reaction mixture was then sealed
  3. concentrationThe reaction mixture was concentrated
  4. customFlash chromatography (CH2Cl2 : MeOH: NH4OH (94.75/3.5/1.75)) followed by crystallization from THF and petroleum ether

Sources & evidence

ORD record
ord-8b451d7eb3a841c195882c577903ea0e
Source dataset
uspto-grants-1996_03
Patent number
US05500442

Reaction notes

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