Diisopropylethylamine → 5-[3-(4-Thiazol-2-yl-benzylamino)-propyl]-thiophene-2-carboxylic acid methyl ester

HRID 2300442Notes

Reaction equation

HRID 2300442 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][NH2:13])=[CH:8][CH:9]=1)=[O:4].[S:14]1[CH:18]=[CH:17][N:16]=[C:15]1[C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1.C(N(CC)C(C)C)(C)C>>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][NH:13][CH2:23][C:22]2[CH:21]=[CH:20][C:19]([C:15]3[S:14][CH:18]=[CH:17][N:16]=3)=[CH:26][CH:25]=2)=[CH:8][CH:9]=1)=[O:4]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 105356554-(1,3-Thiazol-2-yl)benzaldehydeHCID 19989043Methyl 5-(3-aminopropyl)thiophene-2-carboxylate

Product 1

HCID 537725815-[3-(4-Thiazol-2-yl-benzylamino)-propyl]-thiophene-2-carboxylic acid methyl ester

Procedure

The title compound of Step A was prepared from 5-(3-amino-propyl)-thiophene-2-carboxylic acid methyl ester, of Preparation 5, and 4-thiazol-2-yl-benzaldehyde, of Preparation 25, using the method described in Example 1, Step A, except N,N-diisopropylethylamine was used in place of triethylamine. 1H NMR (400 MHz, CDCl3) δ 8.97-7.32 (m, 7H), 6.72 (d, 1H, J=4 Hz), 3.82 (s, 3H), 3.70 (s, 2H), 2.91 (t, 2H, J=7 Hz), 2.62 (t, 2H, J=7 Hz), 1.90 (m, 2H); MS 373 (M+1).

Sources & evidence

ORD record
ord-0479bb1508a945b48f44e05c54f481dc
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Reaction notes

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