1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178492637, compound

HRID 420125Notes

Reaction equation

HRID 420125 reaction equation
[CH3:1][O:2][N:3]1[C:11]2[C:6](=[C:7]([O:15][CH3:16])[CH:8]=[C:9]([C:12]([OH:14])=O)[CH:10]=2)[CH:5]=[CH:4]1.Cl.[NH:18]1[C:22]([C:23]2[CH:24]=[C:25]3[C:35](=[CH:36][CH:37]=2)[O:34][C:28]2([CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH2:27][C:26]3=[O:38])=[N:21][N:20]=[N:19]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O.C(N(CC)CC)C>[CH3:1][O:2][N:3]1[C:11]2[C:6](=[C:7]([O:15][CH3:16])[CH:8]=[C:9]([C:12]([N:31]3[CH2:32][CH2:33][C:28]4([CH2:27][C:26](=[O:38])[C:25]5[C:35](=[CH:36][CH:37]=[C:23]([C:22]6[NH:21][N:20]=[N:19][N:18]=6)[CH:24]=5)[O:34]4)[CH2:29][CH2:30]3)=[O:14])[CH:10]=2)[CH:5]=[CH:4]1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 666494221,4-dimethoxy-1H-indole-6-carboxylic acidHCID 178479612HCID 178479612, compound

Product 1

HCID 178492637HCID 178492637, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

Triethylamine (310 μl) and water (1.5 mL) were added to a solution of 1,4-dimethoxy-1H-indole-6-carboxylic acid (300 mg), 6-(1H-tetrazol-5-yl)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (478 mg), WSC (311 mg) and HOBT (249 mg) in DMF (6 mL), and stirred at 90° C. for 30 minutes. Water was added thereto at room temperature, and a white precipitate was thus obtained. This was dried under reduced pressure, washed with a mixed solvent of methanol and diethyl ether, and dried again under reduced pressure to obtain the above-described compound as a colorless solid. 1H-NMR (400 MHz, DMSO-d6) δ: 8.41 (1H, d, J=2.2 Hz), 8.23 (1H, dd, J=8.5, 2.2 Hz), 7.63 (1H, d, J=3.4 Hz), 7.33 (1H, d, J=8.5 Hz), 7.11 (1H, s), 6.58 (1H, s), 6.37 (1H, d, J=3.4 Hz), 4.34-4.18 (1H, br m), 4.05 (3H, s), 3.89 (3H, s), 3.73-3.14 (3H, br m), 2.98 (2H, s), 2.15-1.76 (4H, br m); MS [M+H]+=489.

Workup

  1. customat room temperature, and a white precipitate was thus obtained
  2. customThis was dried under reduced pressure
  3. washwashed with a mixed solvent of methanol and diethyl ether
  4. customdried again under reduced pressure

Sources & evidence

ORD record
ord-1c0b728960054ff887856e1f4f023eb5
Source dataset
uspto-grants-2012_01
Patent number
US08093389B2

Reaction notes

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