2-Methoxyphenylacetic acid → HCID 44132109, compound

HRID 452249Notes

Reaction equation

HRID 452249 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.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][C:23]([OH:25])=O.CCN=C=NCCCN(C)C.[ClH:37].[CH:38]1[CH:39]=[CH:40][C:41]2N(O)N=N[C:42]=2[CH:43]=1.C(N(CC)CC)C>ClCCl>[Cl:37][C:38]1[CH:43]=[C:42]2[C:41](=[CH:40][CH:39]=1)[O:3][C:4]1([CH2:5][CH2:6][CH2:7]1)[CH2:9][CH:10]2[NH:12][C:23](=[O:25])[CH2:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[O:15][CH3:14]

Participants

7

Reactant 5

HCID 71342-Methoxyphenylacetic 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 44132109HCID 44132109, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from Intermediate 2 (200 mg, 0.763 mmol) and 2-methoxyphenylacetic acid (190 mg, 1.148 mmol) in presence of EDCI.HCl (219 mg, 1.148 mmol), HOBt (175 mg, 1.148 mmol) and triethylamine (318 μl, 2.289 mmol) in dichloromethane (10 ml) as described in Example 1 for 6 h to give 206 mg of the product as a white solid; IR (KBr) 3272, 2979, 1634, 1475, 1248, 753 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.65-1.74 (m, 2H), 1.85-2.04 (m, 2H), 2.12-2.20 (m, 2H), 2.24-2.38 (m, 2H), 3.62 (q, J=14.7 Hz, 2H), 3.85 (s, 3H), 5.19 (q, J=9.3 Hz, 1H), 5.78 (d, J=8.4 Hz, 1H), 6.67 (d, J=8.7 Hz, 1H), 6.87-6.94 (m, 3H), 7.02 (d, J=8.4 Hz, 1H), 7.26-7.30 (m, 2H); ESI-MS (m/z) 372.50 (M+H)+.

Sources & evidence

ORD record
ord-01ee8bde2cc7431b90eb80099d614766
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

Loading…