Veratric Acid → HCID 56598175, compound

HRID 1524298Notes

Reaction equation

HRID 1524298 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.Cl.[CH3:28][N:29]1[CH2:34][CH2:33][C:32]2[N:35]=[C:36]([NH:38][C:39](=[O:51])[C:40]3[CH:45]=[CH:44][CH:43]=[C:42]([CH:46]4[CH2:50][CH2:49][CH2:48][NH:47]4)[CH:41]=3)[S:37][C:31]=2[CH2:30]1.CCN(CC)CC>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([N:47]1[CH2:48][CH2:49][CH2:50][CH:46]1[C:42]1[CH:41]=[C:40]([CH:45]=[CH:44][CH:43]=1)[C:39]([NH:38][C:36]1[S:37][C:31]2[CH2:30][N:29]([CH3:28])[CH2:34][CH2:33][C:32]=2[N:35]=1)=[O:51])=[O:8]

Participants

6

Reactant 4

HCID 7121Veratric AcidHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 87091149HCID 87091149, compound

Product 1

HCID 56598175HCID 56598175, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Stir a solution of 3,4-dimethoxybenzoic acid (49 mg, 0.265 mmol) and CDI (44 mg, 0.265 mmol) in DMF (2.5 mL) for 10 min at room temperature. Add the N-(5-Methyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-yl)-3-pyrrolidin-2-yl-benzamide di-HCl (100 mg, 0.241 mmol) followed by Et3N (0.118 mL, 0.844 mmol), and stir the solution at room temperature for 24 h. Purify the crude reaction by reverse-phase prep-HPLC (10% to 90% CH3CN/water). Concentrate the fractions containing product to give the title compound as a solid (100 mg). MS, electrospray 507.5 (M+H), rt 1.13 min.

Workup

  1. customPurify the crude
  2. customreaction by reverse-phase prep-HPLC (10% to 90% CH3CN/water)
  3. concentrationConcentrate the fractions
  4. additioncontaining product

Sources & evidence

ORD record
ord-1d1eaa5e95aa4a6486ce979fa14277fe
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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