Methoxyacetic Acid → HCID 10288136, compound

HRID 1244705Notes

Reaction equation

HRID 1244705 reaction equation
CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:20][O:21][CH2:22][C:23]([OH:25])=O.CCN=C=NCCCN(C)C.[NH2:37][C@@H:38]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH2:40][C@H:39]1[NH:47][C:48]([C:50]1[NH:54][C:53]2[C:55]([Cl:59])=[C:56]([Cl:58])[S:57][C:52]=2[CH:51]=1)=[O:49]>C(Cl)Cl>[Cl:58][C:56]1[S:57][C:52]2[CH:51]=[C:50]([C:48]([NH:47][C@@H:39]3[CH2:40][C:41]4[C:46](=[CH:45][CH:44]=[CH:43][CH:42]=4)[C@H:38]3[NH:37][C:23](=[O:25])[CH2:22][O:21][CH3:20])=[O:49])[NH:54][C:53]=2[C:55]=1[Cl:59]

Participants

7

Reactant 5

HCID 12251Methoxyacetic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 11772963HCID 11772963, compound

Product 1

HCID 10288136HCID 10288136, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIPEA (180 μL, 1.05 mmol), HOBT (68 mg, 0.5 mmol), methoxyacetic acid (0.5 mmol, 38 μL) and EDAC (120 mg, 0.63 mmol) were added to a suspension of N-[(1R,2R)-1-amino-2,3-dihydro-1H-inden-2-yl]-2,3-dichloro-4H-thieno[3,2-b]pyrrole-5-carboxamide (Method 8, 240 mg, 0.5 mmol) in anhydrous DCM (7 mL). The reaction was stirred at ambient temperature for approximately 16 h. The volatiles were removed by evaporation under reduced pressure, the residue dissolved in EtOAc (10 mL), washed with water (2×10 mL), brine (10 mL) and dried (MgSO4). The volatiles were removed by evaporation under reduced pressure and the residue was purified by flash column chromatography on SiO2 (1:1 EtOAc:isohexane); the solvent removed by evaporation under reduced presssure and dried to give the title compound (44 mg, 20%) as a white solid.

Workup

  1. customThe volatiles were removed by evaporation under reduced pressure
  2. dissolutionthe residue dissolved in EtOAc (10 mL)
  3. washwashed with water (2×10 mL), brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. customThe volatiles were removed by evaporation under reduced pressure
  6. customthe residue was purified by flash column chromatography on SiO2 (1:1 EtOAc:isohexane)
  7. customthe solvent removed by evaporation under reduced presssure
  8. customdried

Sources & evidence

ORD record
ord-af1586ed370e473899d53a1d21fc42c6
Source dataset
uspto-grants-2006_10
Patent number
US07122567B2

Reaction notes

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