Ethyl Acetoacetate → HCID 66746617, compound

HRID 2047763Notes

Reaction equation

[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH:11]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:3]=1[C:4]#[N:5].O=[C:19]([CH3:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>>[CH2:24]([O:23][C:21]([C:20]1[C:19]([CH3:26])=[N:1][C:2]2[C:3]([C:4]=1[NH2:5])=[C:6]([O:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)[CH:7]=[CH:8][CH:9]=2)=[O:22])[CH3:25]

Participants

Reactant 2

HCID 8868Ethyl Acetoacetate

HCID 66747005HCID 66747005, compound

Product 1

HCID 66746617HCID 66746617, compound

Procedure

Prepared as in Example 2a from 2-amino-6-(cycloheptyloxy)benzonitrile (Example 32b) and ethyl 3-oxobutanoate as a bright yellow solid (72%). 1H NMR (400 MHz, DMSO-d6) δ 1.32 (t, J=8.0 Hz, 3H), 1.49-1.65 (m, 8H), 1.78-1.87 (m, 2H), 2.04-2.10 (m, 2H), 2.53 (s, 3H). 4.31 (q, J=8.0 Hz, 2H), 4.79 (m, 1H), 6.89 (d, J=8.0 Hz, 1H), 7.20 (d, J=8.0 Hz, 1H), 7.49 (t, J=8.0 Hz, 1H), 8.14 (brs, 2H). MS 343 (MH+).

Sources & evidence

ORD record: ord-d95d6a41c01446ff9724a5e03d670f13
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592592B2

Reaction notes

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