4-(1,3-Thiazol-2-yl)benzaldehyde → {3-[(4-Thiazol-2-yl-benzylamino)-methyl]-phenoxy}-acetic Acid Tert-butyl Ester

HRID 2117557Notes

Reaction equation

HRID 2117557 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].[S:18]1[CH:22]=[CH:21][N:20]=[C:19]1[C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=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][CH2:27][C:26]2[CH:25]=[CH:24][C:23]([C:19]3[S:18][CH:22]=[CH:21][N:20]=3)=[CH:30][CH:29]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 105356554-(1,3-Thiazol-2-yl)benzaldehydeHCID 20758042t-Butyl [3-(aminomethyl)phenoxy]acetate

Product 1

HCID 53752425{3-[(4-Thiazol-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-thiazol-2-yl-benzaldehyde, of Preparation 25, following the procedure described in Example 3, Step A except no triethylamine was used. 1H NMR (400 MHz, CDCl3) δ 7.90 (d, 2H), 7.82 (d, 1H), 7.39 (d, 2H), 7.28 (d, 1H), 7.22 (m, 1H), 6.92 (m, 2H), 6.77 (m, 1H), 4.50 (s, 2H), 3.80 (s, 2H), 3.76 (s, 2H), 1.46 (s, 9H); MS 411 (M+1).

Sources & evidence

ORD record
ord-33cb834fa8784db880d09546c5b473d5
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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