Triethylamine → HCID 178515383, compound

HRID 1096880Notes

Reaction equation

HRID 1096880 reaction equation
CCN=C=NCCCN(C)C.Cl.[S:13]1[C:17]([C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][CH:19]=2)=[CH:16][C:15]2[CH:27]=[CH:28][CH:29]=[CH:30][C:14]1=2.Cl.[NH:32]1[C:36]([C:37]2[CH:38]=[C:39]3[C:49](=[CH:50][CH:51]=2)[O:48][C:42]2([CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)[CH2:41][C:40]3=[O:52])=[N:35][N:34]=[N:33]1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN1C(=O)CCC1>[S:13]1[C:17]([C:18]2[CH:19]=[CH:20][C:21]([C:22]([N:45]3[CH2:46][CH2:47][C:42]4([CH2:41][C:40](=[O:52])[C:39]5[C:49](=[CH:50][CH:51]=[C:37]([C:36]6[NH:35][N:34]=[N:33][N:32]=6)[CH:38]=5)[O:48]4)[CH2:43][CH2:44]3)=[O:24])=[CH:25][CH:26]=2)=[CH:16][C:15]2[CH:27]=[CH:28][CH:29]=[CH:30][C:14]1=2

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 41373834-Benzo[b]thien-2-ylbenzoic acidHCID 178479612HCID 178479612, compound

Product 1

HCID 178515383HCID 178515383, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

WSC hydrochloride (69.0 mg, 0.36 mmol) was added to a mixture of 4-(benzo[b]thiophen-2-yl)benzoic acid (76.3 mg, 0.300 mmol), 6-(tetrazol-5-yl)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (96.5 mg, 0.300 mmol), HOBT (45.9 mg, 0.300 mmol), triethylamine (0.042 mL, 0.300 mmol) and NMP (1.5 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: 8.44 (1H, d J=2.2 Hz), 8.25 (11, dd, J=8.5, 2.2 z), 8.00 (1H, d, J=8.3 Hz), 7.96 (1H, s), 7.89-7.83 (3H, m), 7.54 (2H, d, J=7.8 Hz), 7.44-7.33 (3H, m), 4.37-4.18 (1H, m), 3.65-3.18 (3H, m), 3.00 (2H, s), 2.13-1.75 (4H, m). MS [M−H]−=520.

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-689aa801f9224d629b31e5cab91cea33
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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