1-Naphthaleneacetic Acid → HCID 44132436, compound

HRID 452255Notes

Reaction equation

HRID 452255 reaction equation
[C:1]1([CH2:11][C:12]([OH:14])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.CCN=C=NCCCN(C)C.[ClH:26].[CH:27]1[CH:28]=[CH:29][C:30]2N(O)N=N[C:31]=2[CH:32]=1.C([N:39]([CH2:42][CH3:43])CC)C.[CH2:44]1[CH2:48][O:47][CH2:46][CH2:45]1>>[Cl:26][C:28]1[CH:29]=[C:30]2[C:31]([CH:42]([NH:39][C:12](=[O:14])[CH2:11][C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)[CH2:43][C:48]3([O:47]2)[CH2:44][CH2:45][CH2:46]3)=[CH:32][CH:27]=1

Participants

6

Reactant 5

HCID 68621-Naphthaleneacetic AcidHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 44132436HCID 44132436, compound

Procedure

The title compound was prepared from Intermediate 10 (200 mg, 0.761 mmol) and 1-naphthylacetic acid (171 mg, 0.913 mmol) in presence of EDCI.HCl (221 mg, 1.141 mmol), HOBt (176 mg, 1.141 mmol) and triethylamine (317 μl, 2.283 mmol) in THF (5 ml) as described in Example 1 to give 250 mg of the product as a white solid; IR (KBr) 3236, 2945, 1638, 1412, 1223, 788 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.47-1.55 (m, 2H), 1.72-1.78 (m, 2H), 2.09 (t, J=7.8 Hz, 3H), 2.16-2.26 (m, 1H), 4.09 (q, J=6.9 Hz, 2H), 5.11-5.19 (m, 1H), 5.29 (d, J=8.4 Hz, 1H), 6.55 (s, 2H), 6.66 (s, 1H), 7.35-7.42 (m, 2H), 7.49-7.59 (m, 2H), 7.77 (d, J=7.2 Hz, 1H), 7.82 (d, J=7.8 Hz, 1H), 7.98 (d, J=7.8 Hz, 1H); APCI-MS (m/z) 392.12 (M+H)+.

Sources & evidence

ORD record
ord-df619f6e69e340348f58c753e1ddee78
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

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