Triethylamine → HCID 178483335, compound

HRID 2183374Notes

Reaction equation

HRID 2183374 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8](C1CCCCO1)[N:7]=[C:6]2[C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21](O)=[O:22])#[N:2].Cl.[NH2:28][CH:29]1[CH2:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30]1.C1C=CC2N(O)[N:45]=[N:44]C=2C=1.CCN=C=NC[CH2:54][CH2:55][N:56]([CH3:58])[CH3:57].Cl.C(N(CC)CC)C>C1COCC1.CN(C=O)C>[CH3:58][N:56]([CH2:55][C:54]1[N:2]=[C:1]([C:3]2[CH:4]=[C:5]3[C:9](=[CH:10][CH:11]=2)[NH:8][N:7]=[C:6]3[C:18]2[CH:19]=[C:20]([C:21]([NH:28][CH:29]3[CH2:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH2:30]3)=[O:22])[CH:24]=[CH:25][CH:26]=2)[NH:45][N:44]=1)[CH3:57]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 1227642-Aminoindan hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22480305HCID 22480305, compound

Product 1

HCID 178483335HCID 178483335, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared in a similar fashion to that of Example 367 A using the following amounts of reagents: 3-(5-cyano-1-perhydro-2H-pyran-2-yl-1H-indazol-3-yl)benzoic acid (800 mg, 2.29 mmol), 2-aminoindan hydrochloride (652 mg, 3.84 mmol), HOBT (931 mg, 6.89 mmol), EDAC.HCl (1.32 g, 6.89 mmol) and triethylamine (535 gL, 3.85 mmol) in anhydrous THF (20.0 mL) and anhydrous DMF (7.0 mL). Precipitation from methanol and ethyl acetate with hexanes afforded the desired compound (824 mg, 78% yield) as an off-white powder 1H NMR (DMSO-d6) δ 8.87 (d, 1H), 8.7 (s, 1H), 8.39 (s, 1H), 8.16 (d, 1H), 8.02 (d, 1H), 7.94 (d, 1H), 7.84 (dd, 1H), 7.62 (t, 1H), 7.3-7.1 (m, 4H), 6.02 (dd, 1H), 4.78-4.7 (m,1H), 3.9-3.7 (m, 2H), 3.27 (dd, 2H), 2.98 (dd, 2H), 2.1-1.5 (m, 6H).

Workup

  1. customThe title compound was prepared in a similar fashion to that of Example 367 A using the following amounts of reagents
  2. customPrecipitation from methanol and ethyl acetate with hexanes

Sources & evidence

ORD record
ord-1743583d694f44f282e83a804dde455d
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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