Triethylamine → HCID 68792030, compound

HRID 452264Notes

Reaction equation

HRID 452264 reaction equation
CC1(C)C[CH:10]([NH2:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7]C=2)[O:3]1.[CH:14]([S:17]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1/[CH:27]=[CH:28]/[C:29]([OH:31])=O)(=[O:19])=[O:18])([CH3:16])[CH3:15].CCN=C=NCCCN(C)C.[ClH:43].[CH:44]1[CH:45]=[CH:46][C:47]2N(O)N=N[C:48]=2[CH:49]=1.C(N(CC)CC)C>ClCCl>[Cl:43][C:44]1[CH:49]=[C:48]2[C:47](=[CH:46][CH:45]=1)[O:3][C:4]1([CH2:5][CH2:6][CH2:7]1)[CH2:9][CH:10]2[NH:12][C:29](=[O:31])/[CH:28]=[CH:27]/[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[NH:20][S:17]([CH:14]([CH3:15])[CH3:16])(=[O:18])=[O:19]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 153387052,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-amineHCID 68792991HCID 68792991, compound

Product 1

HCID 68792030HCID 68792030, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound was prepared from Intermediate 2 (150 mg, 0.576 mmol) and (2E)-3-{2-[(isopropylsulfonyl)amino]phenyl}acrylic acid (186 mg, 0.692 mmol) in presence of EDCI.HCl (165 mg, 0.865 mmol), HOBt (132 mg, 0.865 mmol) and triethylamine (240 μl, 1.732 mmol) in dichloromethane (10 ml) as described in Example 1 to give 125 mg of the product as a white solid; 1H NMR (300 MHz, CDCl3) δ 0.82-0.90 (m, 2H), 1.20-1.26 (m, 4H), 1.74-1.85 (m, 3H), 2.10-2.20 (m, 3H), 2.46-2.52 (m, 2H), 3.29 (t, J=6.3 Hz, 1H), 3.34-3.40 (m, 1H), 6.00-6.06 (m, 1H), 6.40 (d, J=15.6 Hz, 1H), 6.72 ((d, J=8.4 Hz, 1H), 7.05-7.18 (m, 3H), 7.33 (d, J=7.8 Hz, 2H), 7.49 (d, J=7.5 Hz, 1H), 7.57 (d, J=7.8 Hz, 1H), 8.08 (d, J=15.9 Hz, 1H).

Sources & evidence

ORD record
ord-b9e6db0b5392495ea2354572f6bfa2bf
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

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