Triethylamine → HCID 44132600, compound

HRID 452260Notes

Reaction equation

HRID 452260 reaction equation
C[C:2]1([CH3:13])[CH2:11][CH:10](N)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[O:3]1.[O:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[C:22](CC(O)=O)[C:17]=2[O:16][CH2:15]1.CCN=C=NCCCN(C)C.[ClH:38].C1C=CC2N([OH:48])N=NC=2C=1.C([N:51]([CH2:54][CH3:55])[CH2:52][CH3:53])C>ClCCl>[O:16]1[C:17]2[CH:22]=[CH:21][C:20]([CH2:55][C:54]([NH:51][CH:52]3[C:53]4[C:4](=[CH:5][CH:6]=[C:7]([Cl:38])[CH:8]=4)[O:3][C:2]4([CH2:11][CH2:10][CH2:9]4)[CH2:13]3)=[O:48])=[CH:19][C:18]=2[O:14][CH2:15]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 100581101,3-benzodioxol-4-ylacetic acidHCID 153387052,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-amine

Product 1

HCID 44132600HCID 44132600, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from Intermediate 2 (200 mg, 0.892 mmol) and 1,3-benzodioxol-4-ylacetic acid (161 mg, 0.881 mmol) in presence of EDCI.HCl (256 mg, 1.343 mmol), HOBt (205 mg, 1.343 mmol) and triethylamine (366 μl, 2.683 mmol) in dichloromethane (10 ml) as described in Example 1 to give 125 mg of the product as a white solid; IR (KBr) 3059, 2941, 1634, 1488, 1243, 1045 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.63-1.72 (m, 2H), 1.83-1.89 (m, 1H), 2.00-2.07 (m, 1H), 2.12-2.18 (m, 2H), 2.25-2.38 (m, 2H), 3.55 (d, J=2.4 Hz, 2H), 5.21 (q, J=9.9 Hz, 1H), 5.49 (d, J=8.1 Hz, 1H), 5.94 (s, 2H), 6.68-6.76 (m, 4H), 6.93 (s, 1H), 7.04 (dd, J=2.4, 6.3 Hz, 1H); ESI-MS (m/z) 384.16 (M−H)−.

Sources & evidence

ORD record
ord-97d39799372f43eea48b74b97a55307d
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

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