Water → HCID 19006082, compound

HRID 1742891Notes

Reaction equation

HRID 1742891 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N1[CH:26]=[CH:25]N=C1)(N1C=CN=C1)=[O:16].[CH2:27]([N:29]([CH2:32][CH2:33][CH2:34][NH2:35])[CH2:30][CH3:31])[CH3:28].O.CN([CH:40]=[O:41])C>>[OH2:13].[C:40]([OH:41])(=[O:16])[C:12]([OH:14])=[O:13].[CH2:27]([N:29]([CH2:30][CH3:31])[CH2:32][CH2:33][CH2:34][NH:35][C:40]([C:26]1[CH:25]=[CH:8][C:7]([C:4]2[N:3]=[C:2]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:1][CH:5]=2)=[CH:6][CH:2]=1)=[O:41])[CH3:28]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 61011N,N-Diethyl-1,3-propanediamineHCID 682631,1'-CarbonyldiimidazoleHCID 199793842-(2-Thiazolyl)benzoic acid

Product 1

HCID 19006082HCID 19006082, compound

Procedure

A mixture of the thiazole-benzoic acid XXIX (R=Ph: 1.0 g, 3.6 mM) and carbonyldiimidazole (0.9 g, 5.3 mM) in DMF (8 mL) was stirred for 30 min at room temperature. Diethylaminopropylamine was added to this mixture and the reaction was stirred for 2 hours, followed by the addition of water. The resulting suspension was extracted with several portions of ethyl acetate and the combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residue was treated with hexane and oxalic acid to give the title compound as an oxalate salt: mp 115° C. MS: 394 (MH+). Anal. Calc'd for C23H27N3OS.C2H2O4.H2O: C, 59.86; H,6.23; N,8.38 Found: C, 60.20; H,6.16; N,8.80

Workup

  1. stirringthe reaction was stirred for 2 hours
  2. extractionThe resulting suspension was extracted with several portions of ethyl acetate
  3. dry with materialthe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. additionThe residue was treated with hexane and oxalic acid

Sources & evidence

ORD record
ord-b6c4b65a5913473ea21c2b9b5035e0d0
Source dataset
uspto-grants-1994_08
Patent number
US05342851

Reaction notes

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