1H-Indole-3-propanoic acid → HCID 44134163, compound

HRID 452271Notes

Reaction equation

HRID 452271 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.[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH2:23][CH2:24][C:25]([OH:27])=O)=[CH: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>[Cl:39][C:40]1[CH:45]=[C:44]2[C:43](=[CH:42][CH:41]=1)[O:3][C:4]1([CH2:5][CH2:6][CH2:7]1)[CH2:9][CH:10]2[NH:12][C:25](=[O:27])[CH2:24][CH2:23][C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[NH:14][CH:15]=1

Participants

7

Reactant 5

HCID 37441H-Indole-3-propanoic acidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 153387052,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-amine

Product 1

HCID 44134163HCID 44134163, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from Intermediate 2 (200 mg, 0.894 mmol) and 3-(1H-indol-3-yl)propanoic acid (187 mg, 0.988 mmol) in presence of EDCI.HCl (258 mg, 1.345 mmol), HOBt (206 mg, 1.345 mmol) and triethylamine (375 μl, 2.684 mmol) in dichloromethane (10 ml) as described in Example 1 to give 121 mg of the product as a white solid; IR (KBr) 3395, 2926, 1642, 1474, 1234, 748 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.78-1.96 (m, 2H), 2.09-2.26 (m, 6H), 2.63 (t, J=6.3 Hz, 2H), 3.17-3.21 (m, 2H), 5.15 (q, J=9.6 Hz, 1H), 5.34 (d, J=8.4 Hz, 1H), 6.65 (d, J=8.7 Hz, 1H), 6.77 (s, 1H), 6.99-7.14 (m, 4H), 7.35 (d, J=7.8 Hz, 1H), 7.59 (d, J=7.8 Hz, 1H), 8.05 (s, 1H); ESI-MS (m/z) 395.63 (M+H)+.

Sources & evidence

ORD record
ord-58338ac07ab348599856c088870bb74a
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

Loading…