Triethylamine → HCID 44133613, compound

HRID 452267Notes

Reaction equation

HRID 452267 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]([O:17][C:18]1[C:23]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:29][CH2:30][C:31]([OH:33])=O)([CH3:16])[CH3:15].CCN=C=NCCCN(C)C.[ClH:45].[CH:46]1[CH:47]=[CH:48][C:49]2N(O)N=N[C:50]=2[CH:51]=1.C(N(CC)CC)C>ClCCl>[Cl:45][C:46]1[CH:51]=[C:50]2[C:49](=[CH:48][CH:47]=1)[O:3][C:4]1([CH2:5][CH2:6][CH2:7]1)[CH2:9][CH:10]2[NH:12][C:31](=[O:33])[CH2:30][CH2:29][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]([NH:24][S:25]([CH3:28])(=[O:26])=[O:27])[C:18]=1[O:17][CH:14]([CH3:15])[CH3:16]

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 68630033HCID 68630033, compound

Product 1

HCID 44133613HCID 44133613, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from Intermediate 2 (100 mg, 0.384 mmol) and 3-{2-isopropoxy-3-[(methylsulfonyl)amino]phenyl}propanoic acid (116 mg, 0.384 mmol) in presence of EDCI.HCl (111 mg, 0.576 mmol), HOBt (59 mg, 0.384 mmol) and triethylamine (134 μl, 0.961 mmol) in dichloromethane (5 ml) as described in Example 1 to give 122 mg of the product as a white solid; IR (KBr) 3331, 2950, 1645, 1473, 1140, 984 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.35 (d, J=4.8 Hz, 6H), 1.65-1.72 (m, 2H), 1.89-1.95 (m, 1H), 2.10-2.18 (m, 3H), 2.31-2.38 (m, 2H), 2.59 (t, J=7.5 Hz, 2H), 3.00 (s, 5H), 4.22-4.28 (m, 1H), 5.21 (q, J=6.3 Hz, 1H), 5.60 (d, J=8.7 Hz, 1H), 6.71 (d, J=9.0 Hz, 1H), 6.86 (s, 1H), 6.95 (d, J=9.3 Hz, 2H), 7.01-7.08 (m, 2H), 7.37 (d, J=7.2 Hz, 1H); ESI-MS (m/z) 507.39 (M+H)+.

Sources & evidence

ORD record
ord-bf6c1586aca84488b11a0b8f099987a0
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

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