tert-butyl 4-[(1S)-1-aminoethyl]benzoate → tert-Butyl 4-[(1S)-1-({[5-chloro-2-(3-cyanophenoxy)pyridin-3-yl]carbonyl}amino)ethyl]benzoate

HRID 1293188Notes

Reaction equation

HRID 1293188 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[CH:13]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[NH2:20][C@H:21]([C:23]1[CH:35]=[CH:34][C:26]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:25][CH:24]=1)[CH3:22]>>[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([NH:20][C@H:21]([C:23]2[CH:35]=[CH:34][C:26]([C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])=[CH:25][CH:24]=2)[CH3:22])=[O:9])[C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[CH:13]=2)=[N:4][CH:3]=1

Participants

3

Reactant 2

HCID 51358470tert-butyl 4-[(1S)-1-aminoethyl]benzoateHCID 575722665-Chloro-2-(3-cyanophenoxy)nicotinic acid

Product 1

HCID 57572262tert-Butyl 4-[(1S)-1-({[5-chloro-2-(3-cyanophenoxy)pyridin-3-yl]carbonyl}amino)ethyl]benzoate

Procedure

The title compound was prepared according to the procedure described in step 3 of Example 1 from 5-chloro-2-(3-cyanophenoxy)nicotinic acid (step 1) and tert-butyl 4-[(1S)-1-aminoethyl]benzoate (step 3 of Example 44): 1H-NMR (CDCl3) δ 8.56 (1H, d, J=2.7 Hz), 8.13 (1H, d, J=2.7 Hz), 7.98–7.95 (2H, m), 7.89–7.86 (1H, m), 7.64–7.38 (6H, m), 5.42–5.31 (1H, m), 1.61–1.58 (12H, m); MS (ESI) m/z 476 (M−H)−.

Sources & evidence

ORD record
ord-e2830b7e235c4b3a9956009f9ee76ba5
Source dataset
uspto-grants-2007_07
Patent number
US07238714B2

Reaction notes

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