Water → HCID 22340135, compound

HRID 585172Notes

Reaction equation

HRID 585172 reaction equation
[C:1]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1.C[Si]([N:28]=[C:29]=[O:30])(C)C.O>CN(C=O)C>[C:1]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:29]([NH2:28])=[O:30])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70696Trimethylsilyl isocyanateHCID 22340137HCID 22340137, compound

Product 1

HCID 22340135HCID 22340135, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To 100 mg (0.33 mmol) of the product of Example 27 step 1 in 15 mL of DMF was added 57 mg (0.50 mmol) of trimethylsilyl isocyanate the solution was heated to 50° C. for 1.5 hr. At the end of this time it was poured into 100 mL of water. The resulting precipitate was collected by filtration and taken up in hot ethyl acetate. The excess water was removed by decantation and the solution allow to cool. Hexane was introduced to cloudiness and the solution allow to cool further to yield 55 mg (48%) of product as a colorless solid, m.p. 143-144° C. NMR (400 MHz, DMSO) δ 8.42 (s, 1H); 7.34 (m, 10H); 7.10 (t, J=7.7 Hz, 1H); 6.73 (d, J=7.7 Hz, 1H); 5.77 (s, 2H); 4.30 (s, 2H); 3.53 (t, J=6.8 Hz, 2H); 2.72 (t, J=6.8 Hz, 2H). Anal. Calcd. for C21H21N O: C, 83.13; H, 6.98; N, 4.62 Found: C, 75.13; H, 6.41; N, 8.11. (+)FAB m/z 347 (M+H), 369 (M+Na).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customThe excess water was removed by decantation
  3. temperatureto cool
  4. additionHexane was introduced to cloudiness
  5. temperatureto cool further

Sources & evidence

ORD record
ord-22de7e0c2b7b420494c20a818fce687d
Source dataset
uspto-grants-2005_08
Patent number
US06930131B2

Reaction notes

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