Ammonia → HCID 15126104, compound

HRID 2260888Notes

Reaction equation

HRID 2260888 reaction equation
[Si:1]([O:18][CH2:19][C@H:20]1[S:24][CH:23]([N:25]2[CH:33]=[N:32][C:31]3[C:26]2=[N:27][C:28]([Cl:35])=[N:29][C:30]=3Cl)[CH2:22][CH2:21]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:36]>>[Si:1]([O:18][CH2:19][C@H:20]1[S:24][CH:23]([N:25]2[CH:33]=[N:32][C:31]3[C:26]2=[N:27][C:28]([Cl:35])=[N:29][C:30]=3[NH2:36])[CH2:22][CH2:21]1)([C:14]([CH3:15])([CH3:17])[CH3:16])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 22844874HCID 22844874, compound

Product 1

HCID 15126104HCID 15126104, compoundYield 86%

Conditions

Temperature
50 °C

Procedure

A mixture of 12 (150 mg) and saturated ethanolic ammonia (50 mL) was heated at 50° C. in a glass-lined stainless steel pressure vessel for 48 hours. The reaction mixture was evaporated to dryness to afford a syrup which was purified on two silica gel thick plates (Analtech, GF, 1000 μm) that were developed in 99:1CHCl3 -MeOH. The product was eluted with CHCl3 and evaporated. The residue was crystallized from EtOAc-cyclohexane to give pure 15 (125 mg, 86%); mp. 123°-125° C.; FAB MS 524 (M+H)+ ; 1H NMR (CDCl3) δ 8.14 (s, 1, H-8), 7.72 (m, 4, ArH), 7.42 (m, 6, ArH), 6.02 (brs, 2, NH2), 6.16 (m, i'-H), 3.93 (m, 1, 5'-H), 3.84 (m, 1, 5'-H), 3.73 (m, 1, 4'-H), 2.36 (m, 2, 2'-H), 2.18 (m, 1, 3'-H), 1.90 (m, 1, 3'-H), 1.1 (s, 9, t-butyl).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customto afford a syrup which
  3. customwas purified on two silica gel thick plates (Analtech, GF, 1000 μm) that
  4. washThe product was eluted with CHCl3
  5. customevaporated
  6. customThe residue was crystallized from EtOAc-cyclohexane

Sources & evidence

ORD record
ord-17cf0195fd2645ec88271a28073f6c63
Source dataset
uspto-grants-1995_12
Patent number
US05478928

Reaction notes

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