Triethylamine → HCID 44131781, compound

HRID 452277Notes

Reaction equation

HRID 452277 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.[CH:14]1([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:26][CH2:27][CH2:28][C:29]([OH:31])=O)[CH2:18][CH2:17][CH2:16][CH2:15]1.CCN=C=NCCCN(C)C.[ClH:43].[CH:44]1[CH:45]=[CH:46][C:47]2N(O)N=N[C:48]=2[CH:49]=1.C(N(CC)CC)C>ClCCl>[Cl:43][C:44]1[CH:49]=[C:48]2[C:47](=[CH:46][CH:45]=1)[O:3][C:4]1([CH2:5][CH2:6][CH2:7]1)[CH2:9][CH:10]2[NH:12][C:29](=[O:31])[CH2:28][CH2:27][CH2:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[O:19][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 153387052,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-amineHCID 68630655HCID 68630655, compound

Product 1

HCID 44131781HCID 44131781, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from Intermediate 2 (150 mg, 0.579 mmol) and 4-(2-cyclopentyloxyphenyl)butanoic acid (158 mg, 0.639 mmol) in presence of EDCI.HCl (166 mg, 0.863 mmol), HOBt (133 mg, 0.863 mmol) and triethylamine (241 μl, 2.043 mmol) in dichloromethane (5 ml) as described in Example 1 to give 153 mg of the product as a white solid; IR (KBr) 3300, 2943, 1646, 1474, 1238, 749 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.70-2.00 (m, 12H), 2.24-2.41 (m, 7H), 2.64-2.70 (m, 2H), 3.47 (s, 1H), 4.75 (br s, 1H), 5.25 (d, J=6.0 Hz, 1H), 5.50 (d, J=6.9 Hz, 1H), 6.71 (d, J=8.4 Hz, 1H), 6.79-6.85 (m, 2H), 7.05-7.12 (m, 4H); ESI-MS (m/z) 454.30 (M)+.

Sources & evidence

ORD record
ord-6ec80392ddbd4ced97f8935a0323a938
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

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