Methyl 4-(3-chloro-4,5-bis(cyclohexyloxy)benzamido)benzoate → HCID 67042184, compound

HRID 62736Notes

Reaction equation

HRID 62736 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([O:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[C:20]=1[O:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[C:5]([NH:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=1)=[O:6]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([O:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[C:20]=1[O:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([OH:14])=[O:13])=[CH:16][CH:17]=1)=[O:6]

Participants

3

Reactant 1

HCID 67041755Methyl 4-(3-chloro-4,5-bis(cyclohexyloxy)benzamido)benzoate

Product 1

HCID 67042184HCID 67042184, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-(3-Chloro-4,5-bis(cyclohexyloxy)benzamido)benzoic acid (AAA-047) (15 mg, 19%) was prepared from methyl 4-(3-chloro-4,5-bis(cyclohexyloxy)benzamido)benzoate (8) (80 mg, 0.17 mmol) using a procedure essentially the same as in Step (ii) for AAA-001, except that 1,4-dioxane (6 mL) was used instead of THF: m/z 470 [M−H]− (ES−); 1H NMR (400 MHz, DMSO-d6) δ: 12.72 (1H, br s), 10.44 (1H, s), 7.94 (2H, d), 7.87 (2H, d), 7.67 (1H, d), 7.53 (1H, d), 4.53 (1H, m), 4.36 (1H, m), 1.98-1.82 (4H, m), 1.80-1.65 (4H, m), 1.58-1.20 (12H, m).

Sources & evidence

ORD record
ord-13f0205c9fef407fb0b2b0197deb11c7
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

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