4-(Pyrimidin-2-yl)benzaldehyde → {3-[(4-Pyrimidin-2-yl-benzylamino)-methyl]-phenoxy}-acetic acid tert-butyl ester

HRID 2300520Notes

Reaction equation

HRID 2300520 reaction equation
[C:1]([O:5][C:6](=[O:17])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH2:16])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[N:18]1[CH:23]=[CH:22][CH:21]=[N:20][C:19]=1[C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1>C(N(CC)CC)C>[C:1]([O:5][C:6](=[O:17])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH:16][CH2:28][C:27]2[CH:26]=[CH:25][C:24]([C:19]3[N:18]=[CH:23][CH:22]=[CH:21][N:20]=3)=[CH:31][CH:30]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 127037224-(Pyrimidin-2-yl)benzaldehydeHCID 20758042t-Butyl [3-(aminomethyl)phenoxy]acetate

Product 1

HCID 18376223{3-[(4-Pyrimidin-2-yl-benzylamino)-methyl]-phenoxy}-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The title compound of Step A was prepared from (3-aminomethyl-phenoxy)-acetic acid tert-butyl ester, of Preparation 20, and 4-pyrimidin-2-yl-benzaldehyde, of Preparation 21, using the method described in Example 3, Step A, except no triethylamine was used. 1H NMR (400 MHz, CDCl3) δ 8.89 (d, 2H), 8.38 (d, 2H), 7.46 (d, 2H), 7.23 (m, 1H), 7.17 (m, 1H), 6.95 (m, 2H), 6.78 (dd, 1H), 4.51 (s, 2H), 3.86 (s, 2H), 3.79 (s, 2H), 1.47 (s, 9H); MS 406 (M+1).

Sources & evidence

ORD record
ord-4515b3c15e674b19a2599904213c32f2
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Reaction notes

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