Triethylamine → ASN 06744166

HRID 1519005Notes

Reaction equation

HRID 1519005 reaction equation
CCN=C=NCCCN(C)C.Cl.[C:13]([OH:23])(=O)[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1.C(N(CC)CC)C.[NH2:31][CH2:32][CH2:33][NH:34][C:35]1[C:44]([C:45]#[N:46])=[CH:43][C:42]2[C:37](=[CH:38][C:39]([CH3:48])=[CH:40][C:41]=2[CH3:47])[N:36]=1>C(Cl)Cl>[C:45]([C:44]1[C:35]([NH:34][CH2:33][CH2:32][NH:31][C:13](=[O:23])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)=[N:36][C:37]2[C:42]([CH:43]=1)=[C:41]([CH3:47])[CH:40]=[C:39]([CH3:48])[CH:38]=2)#[N:46]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 114613-Methoxybenzoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3338585HCID 3338585, compound

Product 1

HCID 3224090ASN 06744166Yield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

EDC hydrochloride (0.192 g, 1 mmol), m-anisic acid (0.152 g, 1 mmol) and triethylamine (0.14 mL, 2.5 mmol) were dissolved in dry DCM (10 mL). The reaction was stirred at room temperature for 30 min. Carbonitrile 4 (0.201 g, 1 mmol) dissolved in 5 mL dry DCM was added dropwise to the solution and reaction stirred for 18 h. The reaction was diluted with DCM (50 mL) and washed with 1M NaHSO4 (aq, 2×100 mL). Organics were dried over Na2SO4, filtered and solvent was removed under reduced pressure. The crude product was then purified by flash chromatography (4:1 hexane:ethyl acetate mobile phase) to produce a light yellow solid (Compound 22) in 73% yield. 1H NMR (400 MHz, CDCl3) δ 8.35 (s, 1H), 8.13 (s, 1H), 7.32 (s, 1H), 7.28 (s, 1H), 7.20 (d, J=7.5, 1H), 7.13 (t, J=7.8, 1H), 6.98 (s, 1H), 6.95 (d, J=8.1, 1H), 5.82 (s, 1H), 3.91 (q, J=5.3, 2H), 3.79-3.68 (m, 5H), 2.55 (s, 3H), 2.42 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 168.10, 159.87, 155.10, 144.27, 140.97, 136.27, 135.41, 129.42, 127.13, 124.48, 119.35, 119.23, 117.72, 116.87, 112.46, 94.30, 55.49, 43.39, 41.25, 29.92, 22.21, 18.57. IR (neat): 3380, 3357, 2957, 2925, 2217, 1605, 1583, 1535, 1258. ESI-LCMS m/z [M+H]+=375.18.

Workup

  1. additionwas added dropwise to the solution and reaction
  2. stirringstirred for 18 h
  3. washwashed with 1M NaHSO4 (aq, 2×100 mL)
  4. dry with materialOrganics were dried over Na2SO4
  5. filtrationfiltered
  6. customsolvent was removed under reduced pressure
  7. customThe crude product was then purified by flash chromatography (4:1 hexane:ethyl acetate mobile phase)

Sources & evidence

ORD record
ord-96cab519ad224eada3b1389b2edddc07
Source dataset
uspto-grants-2015_07
Patent number
US09073863B2

Reaction notes

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