Dichloromethane → HCID 21985551, compound

HRID 9176Notes

Reaction equation

HRID 9176 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[CH:15]=[C:14]([C:16]([OH:18])=O)[CH:13]=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].Cl[CH2:20]Cl.Cl.C(N=C=N[CH2:28][CH2:29][CH2:30][N:31](C)C)C.C(N([CH2:39][CH3:40])CC)C>>[C:30]1([NH:31][C:16]([C:14]2[CH:13]=[CH:12][C:10]3[N:11]=[C:7]([NH:6][C:4]([NH:3][CH2:1][CH3:2])=[O:5])[S:8][C:9]=3[CH:15]=2)=[O:18])[CH:29]=[CH:28][CH:40]=[CH:39][CH:20]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 653487762-[(Ethylamino)Carbonyl]amino-1,3-benzothiazole-6-carboxylic acid

Product 1

HCID 21985551HCID 21985551, compound

Procedure

About 0.2 g of 2-[(ethylamino)Carbonyl]amino-1,3-benzothiazole-6-carboxylic acid was dissolved into about 20 mL dichloromethane and about 0.2 mL triethylamine. Added about 1 eq of the appropriate amine followed by about 0.3 g of 1-ethyl-3-(3-dimethylaminopropyl)Carbodiimide hydrochloride then stirred at room temperature for about 12–24 hours. The solvent was removed under reduced pressure then the crude reaction mixture was purified by preparative HPLC. 1H NMR 1.10 (t, 3H), 3.2 (m, 2H), 6.76 (br s, 11), 7.10 (m, 1H), 7.36 (m, 2H), 7.70 (d, 1H), 7.79 (d, 2H), 7.97 (m, 1H), 8.5 (s, 1H), 10.23 (s, 1H), 10.9 (br s, 1H); LC/MS 2.86 min, 341 (M+1);

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude reaction mixture
  3. customwas purified by preparative HPLC
  4. customLC/MS 2.86 min, 341 (M+1)

Sources & evidence

ORD record
ord-7e0ae6c8d873495eb76902d9b21f0789
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Reaction notes

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