Triethylamine → Methyl 3-(2-(3-(benzyloxy)-5-bromopyridin-2-ylamino)thiazol-4-yl)propanoate

HRID 1426135Notes

Reaction equation

HRID 1426135 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([NH:16][C:17]([NH2:19])=[S:18])=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:21][C:22](=O)[CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26].C(N(CC)CC)C>CO>[CH2:1]([O:8][C:9]1[C:10]([NH:16][C:17]2[S:18][CH:21]=[C:22]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])[N:19]=2)=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9855825Methyl 5-bromo-4-oxopentanoateHCID 727056401-(3-(Benzyloxy)-5-bromopyridin-2-yl)thiourea

Product 1

HCID 16660673Methyl 3-(2-(3-(benzyloxy)-5-bromopyridin-2-ylamino)thiazol-4-yl)propanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(3-(Benzyloxy)-5-bromopyridin-2-yl)thiourea (2.00 g, 5.91 mmol), methyl 5-bromo-4-oxopentanoate (1.48 g, 7.10 mmol) (prepared according to Synthetic Communications (1994) 2557-2562), and triethylamine (1.44 mL, 10.3 mmol) were heated in methanol (50 mL) at reflux for 3 hours according to the method of Example 2, Step C, to provide methyl 3-(2-(3-(benzyloxy)-5-bromopyridin-2-ylamino)thiazol-4-yl)propanoate as a light yellow powder. 1H NMR (DMSO-d6) δ 10.26 (bs, 1H), 7.97 (s, 1H), 7.35-7.63 (m, 6H), 6.66 (bs, 1H), 5.29 (s, 2H), 3.59 (s, 3H), 2.85 (t, 2H), 2.69 (t, 2H). Mass spectrum (esi) m/z=448 (96), 450 (100).

Workup

  1. temperatureat reflux for 3 hours

Sources & evidence

ORD record
ord-2a7c37b1eac04cd4a7e65eba9fb2e89d
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

Loading…