Triethylamine → HCID 131726358, compound

HRID 1273023Notes

Reaction equation

HRID 1273023 reaction equation
C([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1)[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.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=[N:44][C:42]=2C=1.CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>C1COCC1.CN(C=O)C>[C:42]([CH:15]1[CH2:14][O:13][CH:12]([N:8]2[C:9]3[C:5](=[CH:4][CH:3]=[CH:11][CH:10]=3)[C:6]([C:18]3[CH:19]=[C:20]([C:21]([NH:28][CH:29]4[CH2:37][C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[CH2:30]4)=[O:22])[CH:24]=[CH:25][CH:26]=3)=[N:7]2)[CH2:17][CH2:16]1)#[N:44]

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 131726358HCID 131726358, 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 μL, 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-3c28263fb59d4c6f8cc7c5c64badd3a9
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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