Triethylamine → HCID 44131603, compound

HRID 452274Notes

Reaction equation

HRID 452274 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:18]2[CH:19]=[CH:20][CH:21]=[C:22]([CH2:23][CH2:24][C:25]([OH:27])=O)[C:17]=2[O:16][CH2:15]1.CCN=C=NCCCN(C)C.[ClH:39].[CH:40]1[CH:41]=[CH:42][C:43]2N(O)N=N[C:44]=2[CH:45]=1.C(N(CC)CC)C>ClCCl>[O:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[C:22]([CH2:23][CH2:24][C:25]([NH:12][CH:10]3[C:43]4[C:44](=[CH:45][CH:40]=[C:41]([Cl:39])[CH:42]=4)[O:3][C:4]4([CH2:5][CH2:6][CH2:7]4)[CH2:9]3)=[O:27])[C:17]=2[O:16][CH2:15]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2319813-(1,3-benzodioxol-4-yl)propanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 153387052,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-amine

Product 1

HCID 44131603HCID 44131603, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from Intermediate 2 (150 mg, 0.679 mmol) and 3-(1,3-benzodioxol-4-yl)propanoic acid (169 mg, 0.892 mmol) in presence of EDCI.HCl (192 mg, 1.005 mmol), HOBt (154 mg, 1.005 mmol) and triethylamine (135 μl, 1.341 mmol) in dichloromethane (10 ml) as described in Example 1 to give 137 mg of the product as a white solid; IR (KBr) 3314, 2940, 1640, 1456, 1243, 1064 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.63-1.72 (m, 2H), 1.85-1.89 (m, 1H), 2.04-2.17 (m, 3H), 2.27-2.37 (m, 2H), 2.58 (t, J=6.9 Hz, 2H), 2.96-3.02 (m, 2H), 5.20 (q, J=9.3 Hz, 1H), 5.54 (d, J=8.7 Hz, 1H), 5.87 (d, J=8.7 Hz, 2H), 6.69-6.80 (m, 4H), 6.92 (s, 1H), 7.05 (d, J=8.7 Hz, 1H).

Sources & evidence

ORD record
ord-dddb726505664d459f622c8185eceaf2
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

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