Triethylamine → HCID 68791685, compound

HRID 452275Notes

Reaction equation

HRID 452275 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.[O:14]1[C:19]2[CH:20]=[CH:21][CH:22]=[C:23]([CH2:24][CH2:25][C:26]([OH:28])=O)[C:18]=2[O:17][CH2:16][CH2:15]1.CCN=C=NCCCN(C)C.[ClH:40].[CH:41]1[CH:42]=[CH:43][C:44]2N(O)N=N[C:45]=2[CH:46]=1.C(N(CC)CC)C>ClCCl>[O:14]1[C:19]2[CH:20]=[CH:21][CH:22]=[C:23]([CH2:24][CH2:25][C:26]([NH:12][CH:10]3[C:44]4[C:45](=[CH:46][CH:41]=[C:42]([Cl:40])[CH:43]=4)[O:3][C:4]4([CH2:5][CH2:6][CH2:7]4)[CH2:9]3)=[O:28])[C:18]=2[O:17][CH:16]=[CH:15]1

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 17774216HCID 17774216, compound

Product 1

HCID 68791685HCID 68791685, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from Intermediate 2 (200 mg, 0.769 mmol)) and 3-(2,3-dihydro-1,4-benzodioxin-5-yl)propanoic acid (191 mg, 0.923 mmol) in presence of EDCI.HCl (221 mg, 1.153 mmol), HOBt (176 mg, 1.153 mmol) and triethylamine (321 μl, 2.307 mmol) in dichloromethane (10 ml) as described in Example 1 to give 141 mg of the product as a white solid; IR (KBr) 3276, 2935, 1639, 1474, 1262, 1094 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.63-1.71 (m, 3H), 1.89 (br s, 1H), 2.13-2.27 (m, 2H), 2.33-2.37 (m, 2H), 2.57 (t, J=7.5 Hz, 2H), 2.96 (t, J=6.9 Hz, 2H), 4.19 (d, J=6.3 Hz, 4H), 5.19 (q, J=8.7 Hz, 1H), 5.62 (d, J=8.1 Hz, 1H), 6.69-6.74 (m, 4H), 6.95 (s, 1H), 7.05 (d, J=8.1 Hz, 1H); ESI-MS (m/z) 414.47 (M+H)+.

Sources & evidence

ORD record
ord-84a5006a8ef542c98069945b16d030ba
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

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