Triethylamine → HCID 178492638, compound

HRID 1096883Notes

Reaction equation

HRID 1096883 reaction equation
CCN=C=NCCCN(C)C.Cl.[NH:13]1[C:21]2[C:16](=[CH:17][C:18]([C:22]3[CH:23]=[C:24]([CH:28]=[C:29]([O:31][CH3:32])[CH:30]=3)[C:25](O)=[O:26])=[CH:19][CH:20]=2)[CH:15]=[CH:14]1.Cl.[NH:34]1[C:38]([C:39]2[CH:40]=[C:41]3[C:51](=[CH:52][CH:53]=2)[O:50][C:44]2([CH2:49][CH2:48][NH:47][CH2:46][CH2:45]2)[CH2:43][C:42]3=[O:54])=[N:37][N:36]=[N:35]1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN1C(=O)CCC1.C(Cl)(Cl)Cl>[NH:13]1[C:21]2[C:16](=[CH:17][C:18]([C:22]3[CH:23]=[C:24]([C:25]([N:47]4[CH2:48][CH2:49][C:44]5([CH2:43][C:42](=[O:54])[C:41]6[C:51](=[CH:52][CH:53]=[C:39]([C:38]7[NH:37][N:36]=[N:35][N:34]=7)[CH:40]=6)[O:50]5)[CH2:45][CH2:46]4)=[O:26])[CH:28]=[C:29]([O:31][CH3:32])[CH:30]=3)=[CH:19][CH:20]=2)[CH:15]=[CH:14]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 579309723-(1H-indol-5-yl)-5-methoxybenzoic acidHCID 178479612HCID 178479612, compound

Product 1

HCID 178492638HCID 178492638, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

WSC hydrochloride (52.5 mg, 0.274 mmol) was added to a mixture of 3-(1H-indol-5-yl)-5-methoxybenzoic acid (61.0 mg, 0.228 mmol), 6-(tetrazol-5-yl)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (73.4 mg, 0.228 mmol), HOBT (34.9 mg, 0.228 mmol), triethylamine (0.048 mL, 0.34 mmol), chloroform (0.4 mL) and NMP (0.8 mL), and stirred at room temperature for 20 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified through high-performance preparative liquid chromatography (0.1% TFA, water/acetonitrile) to obtain the title compound as a pale yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ: 11.18 (1H, s), 8.43 (1H, d J=2.3 Hz), 8.25 (1H, dd, J=8.8, 2.3 Hz), 7.87-7.86 (1H, m), 7.47 (1H, d, J=8.4 Hz), 7.41 (1H, dd, J=8.4, 1.7 Hz), 7.39 (1H, t, J=2.8 Hz), 7.35 (1H, d, J=8.8 Hz), 7.26 (1H, dd, J=2.4, 1.5 Hz), 7.24 (1H, t, J=1.5 Hz), 6.87 (1H, dd, J=2.4, 1.5 Hz), 6.49 (1H, ddd, J=2.8, 2.1, 0.7 Hz), 4.37-4.23 (1H, m), 3.86 (3H, s), 3.66-3.18 (3H, m), 2.99 (2.0H, s), 2.14-1.81 (4H, m). MS [M−H]−=533.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified through high-performance preparative liquid chromatography (0.1% TFA, water/acetonitrile)

Sources & evidence

ORD record
ord-e64a538db44a4592ad23ae6921598aa2
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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