Benzoic Acid → HCID 59395612, compound

HRID 1097684Notes

Reaction equation

HRID 1097684 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[Cl:33][C:34]1[NH:42][C:41]2[C:40](=[O:43])[N:39]([CH2:44][CH2:45][CH2:46][CH2:47][C:48](=[NH:51])[NH:49]O)[C:38](=[O:52])[N:37]([CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[C:36]=2[N:35]=1>CS(C)=O>[Cl:33][C:34]1[NH:42][C:41]2[C:40](=[O:43])[N:39]([CH2:44][CH2:45][CH2:46][CH2:47][C:48]3[N:49]=[C:1]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[O:9][N:51]=3)[C:38](=[O:52])[N:37]([CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[C:36]=2[N:35]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 178446222HCID 178446222, compound

Product 1

HCID 59395612HCID 59395612, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Conditions

Temperature
40 °C

Procedure

Benzoic acid (18 mg, 0.15 mmol) was treated with a solution of 1H-1,2,3-benzotriazol-1-ol hydrate (25 mg, 0.19 mmol) in DMSO (0.3 ml). To this was added a solution/suspension of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (29 mg, 0.15 mmol) in DMSO (0.3 ml) followed by a solution of 5-(8-chloro-2,6-dioxo-3-pentyl-2,3,6,7-tetrahydro-1H-purin-1-yl)-N-hydroxypentanimidamide (55 mg, 0.15 mmol) in DMSO (0.3 ml). The mixture was heated at 40° C. for 1 h, then at 80° C. for 5 h and then cooled. The mixture was subjected to purification by MDAP. Product-containing fractions were blown to dryness by a stream of nitrogen to yield the title compound as a white solid (17.2 mg, 25%).

Workup

  1. additionTo this was added
  2. temperaturecooled
  3. customThe mixture was subjected to purification by MDAP

Sources & evidence

ORD record
ord-83c08c36523e4f65b7effb4a9ab20a71
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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