1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 24857133, compound

HRID 420130Notes

Reaction equation

HRID 420130 reaction equation
CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH:22]1([N:25]2[C:33]3[C:28](=[C:29]([O:37][CH2:38][CH3:39])[CH:30]=[C:31]([C:34]([OH:36])=O)[CH:32]=3)[C:27]([CH3:40])=[CH:26]2)[CH2:24][CH2:23]1.Cl.Cl.[O:43]=[C:44]1[C:58]2[C:53](=[CH:54][CH:55]=[C:56]([C:59]3[CH:60]=[N:61][CH:62]=[C:63]([CH:68]=3)[C:64]([O:66]C)=[O:65])[CH:57]=2)[O:52][C:46]2([CH2:51][CH2:50][NH:49][CH2:48][CH2:47]2)[CH2:45]1>CN(C=O)C>[CH:22]1([N:25]2[C:33]3[C:28](=[C:29]([O:37][CH2:38][CH3:39])[CH:30]=[C:31]([C:34]([N:49]4[CH2:50][CH2:51][C:46]5([CH2:45][C:44](=[O:43])[C:58]6[C:53](=[CH:54][CH:55]=[C:56]([C:59]7[CH:60]=[N:61][CH:62]=[C:63]([CH:68]=7)[C:64]([OH:66])=[O:65])[CH:57]=6)[O:52]5)[CH2:47][CH2:48]4)=[O:36])[CH:32]=3)[C:27]([CH3:40])=[CH:26]2)[CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 66649349HCID 66649349, compoundHCID 66649387HCID 66649387, compound

Product 1

HCID 24857133HCID 24857133, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

TEA (162 mg) was added to a mixture of EDCI (92 mg), HOBT (73.5 mg), 1-cyclopropyl-4-ethoxy-3-methyl-1H-indole-6-carboxylic acid (104 mg), and methyl 5-(4-oxospiro[chroman-2,4′-piperidin]-6-yl)nicotinate dihydrochloride (170 mg) and DMF (3 ml), and the mixture was stirred at r.t. for 5 hours. The mixture was evaporated and purified through SiO2 column chromatography (eluted with Hex-EtOAc, then MeOH—CHCl3) to give methyl ester of the title compound as a pale yellow solid. 1 ml of 1N NaOHaq was added to its solution in 3 ml of MeOH and 3 ml of THF, and the mixture was stirred at r.t. for 4 h. Then the mixture was neutralized with 1N HClaq and diluted with CHCl3-MeOH. The mixture was dried over Na2SO4, filtered, and concentrated. The residue was crystallized from EtOAc-n-hexane to give the title compound as a slightly yellowish powder. 1H-NMR (400 MHz, DMSO-d6) δ: 13.57 (1H, s), 9.08 (1H, d, J=2.0 Hz), 9.03 (1H, d, J=2.0 Hz), 8.41 (1H, dd, J=2.0, 2.0 Hz), 8.08-8.02 (2H, m), 7.26 (1H, dd, J=7.8, 1.0 Hz), 7.12 (1H, d, J=1.0 Hz), 7.00 (1H, d, J=1.0 Hz), 6.48 (1H, s), 4.36-4.14 (1H, br m), 4.08 (2H, q, J=7.0 Hz), 3.78-3.20 (4H, br m), 2.96 (2H, s), 2.33 (3H, d, J=1.0 Hz), 2.09-1.73 (4H, m), 1.37 (3H, t, J=7.0 Hz), 1.03-0.98 (2H, m), 0.89-0.85 (2H, m); MS [M+H]+=580.

Workup

  1. customThe mixture was evaporated
  2. custompurified through SiO2 column chromatography (
  3. washeluted with Hex-EtOAc

Sources & evidence

ORD record
ord-90cc3e7e166340d498d77cf9f2142daa
Source dataset
uspto-grants-2012_01
Patent number
US08093389B2

Reaction notes

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