Triethylamine → HCID 44132601, compound

HRID 452261Notes

Reaction equation

HRID 452261 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13](F)[CH:14]=1)[O:11][C:7]1([CH2:10][CH2:9][CH2:8]1)[CH2:6][CH:5]2[NH2:16].[F:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][C:22]([CH2:27][C:28](O)=[O:29])=[C:21]2[CH3:31].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>ClCCl>[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[O:11][C:7]1([CH2:10][CH2:9][CH2:8]1)[CH2:6][CH:5]2[NH:16][C:28](=[O:29])[CH2:27][C:22]1[NH:23][C:24]2[C:20]([C:21]=1[CH3:31])=[CH:19][C:18]([F:17])=[CH:26][CH:25]=2

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59614621HCID 59614621, compoundHCID 86761949HCID 86761949, compound

Product 1

HCID 44132601HCID 44132601, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from Intermediate 6 (200 mg, 0.963 mmol) and (5-fluoro-3-methyl-1H-indol-2-yl)acetic acid (200 mg, 0.963 mmol) in presence of EDCI.HCl (276 mg, 1.145 mmol), HOBt (221 mg, 1.145 mmol) and triethylamine (401 μl, 3.003 mmol) in dichloromethane (10 ml) as described in Example 1 to give 18 mg of the product as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.52-1.74 (m, 4H), 1.88-1.95 (m, 2H), 2.08-2.25 (m, 2H), 2.40 (s, 3H), 3.70 (s, 2H), 5.23 (q, J=8.7 Hz, 1H), 5.68 (d, J=9.0 Hz, 1H), 6.61-6.66 (m, 2H), 6.72-6.89 (m, 2H), 7.07-7.18 (m, 2H), 8.01 (s, 1H); ESI-MS (m/z) 397.33 (M+H)+.

Sources & evidence

ORD record
ord-65175ed396194d19890d5c00d3668238
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

Loading…