Succinic Acid → HCID 71008263, compound

HRID 1630655Notes

Reaction equation

HRID 1630655 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][CH:12]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[OH:13])[C:6]3[CH2:20][CH2:21][N:22]4[CH:26]([C:5]=3[C:4]=2[CH:3]=1)[CH2:25][CH2:24][CH2:23]4.[C:27](O)(=[O:33])[CH2:28][CH2:29][C:30]([OH:32])=[O:31].CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][CH:12]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[O:13][C:27](=[O:33])[CH2:28][CH2:29][C:30]([OH:32])=[O:31])[C:6]3[CH2:20][CH2:21][N:22]4[CH:26]([C:5]=3[C:4]=2[CH:3]=1)[CH2:25][CH2:24][CH2:23]4

Participants

6

Reactant 4

HCID 1110Succinic AcidHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 71007599HCID 71007599, compound

Product 1

HCID 71008263HCID 71008263, compoundYield 21.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(10-Methyl-2,3,5,6-tetrahydro-1H-indolizino[7,8-b]indol-7(11cH)-yl)-1-(pyridin-4-yl)ethanol (350 mg, 1 mmol), succinic acid (118 mg, 1 mmol) and dimethylaminopyridine (122 mg, 1 mmol) in DCM (20 mL) were stirred at RT. Dicyclohexylcarbodiimide (206 mg, 1.6 mmol) in DCM (20 mL) was added dropwise and the reaction mixture was stirred at RT for 2 h. The reaction mixture was concentrated to obtain the crude product that was purified by reverse phase HPLC to yield 4-(2-(10-methyl-2,3,5,6-tetrahydro-1H-indolizino[7,8-b]indol-7(11cH)-yl)-1-(pyridin-4-yl)ethoxy)-4-oxobutanoic acid (96 mg). 1H NMR (CD3OD, freebase) δ (ppm): 8.46 (d, 2H), 7.33 (d, 2H), 7.27 (d, 1H), 7.23 (s, 1H), 7.01 (d, 1H), 6.07 (t, 1H), 4.8 (t, 2H), 4.5 (m, 2H), 3.55 (m, 2H), 3.45 (m, 1H), 3.0 (q, 2H), 2.7 (m, 1H), 2.54 (m, 2H), 2.39 (s, 3H), 2.37 (m, 1H), 2.1 (m, 4H). Separation by chiral HPLC provided diastereomers V-18a-d.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto obtain the crude product that
  3. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-76347f148d4545779872ed4940bd8e8e
Source dataset
uspto-grants-2014_07
Patent number
US08791132B2

Reaction notes

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