Triethylamine → Methyl 3-(2-(3-(benzyloxy)pyridin-2-ylamino)thiazol-4-yl)propanoate

HRID 1426115Notes

Reaction equation

HRID 1426115 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([NH:15][C:16]([NH2:18])=[S:17])=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:20][C:21](=O)[CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25].C(N(CC)CC)C>CO>[CH2:1]([O:8][C:9]1[C:10]([NH:15][C:16]2[S:17][CH:20]=[C:21]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[N:18]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9855825Methyl 5-bromo-4-oxopentanoateHCID 727056391-(3-(Benzyloxy)pyridin-2-yl)thiourea

Product 1

HCID 59225684Methyl 3-(2-(3-(benzyloxy)pyridin-2-ylamino)thiazol-4-yl)propanoateYield 81.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(3-(Benzyloxy)pyridin-2-yl)thiourea (3.30 g, 12.7 mmol), methyl 5-bromo-4-oxopentanoate (3.19 g, 15.3 mmol) (prepared according to Synthetic Communications (1994) 2557-2562), and triethylamine (3.10 mL, 22.3 mmol) were heated in methanol (100 mL) at reflux for 3 hours according to the method of Example 2, Step C, to provide methyl 3-(2-(3-(benzyloxy)pyridin-2-ylamino)thiazol-4-yl)propanoate (3.82 g, 81.3% yield) as a light yellow powder: 1H NMR (DMSO-d6) δ 9.93 (bs, 1H), 7.86 (d, 1H), 7.57 (d, 2H), 7.34-7.42 (m, 4H), 6.89 (m, 1H), 6.63 (s, 1H), 5.26 (s, 2H), 3.60 (s, 3H), 2.85 (t, 2H), 2.69 (t, 2H). Mass spectrum (esi) m/z=370 (100).

Workup

  1. temperatureat reflux for 3 hours

Sources & evidence

ORD record
ord-c9c82c90b8e1491987f68bda868a0ffb
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

Loading…