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

HRID 1426136Notes

Reaction equation

HRID 1426136 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])N=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].[CH2:30](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:30]=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 866396551-(3-(Benzyloxy)-5-bromopyrazin-2-yl)thiourea

Product 1

HCID 16660673Methyl 3-(2-(3-(benzyloxy)-5-bromopyridin-2-ylamino)thiazol-4-yl)propanoateYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(3-(Benzyloxy)-5-bromopyrazin-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 (1.51 g, 57%) as a white powder: 1H NMR (DMSO-d6) δ 11.16 (bs, 1H), 8.02 (s, 1H), 7.59 (d, 2H), 7.36-7.44 (m, 3H), 6.71 (bs, 1H), 5.43 (s, 2H), 3.59 (s, 3H), 2.85 (t, 2H), 2.69 (t, 2H). Mass spectrum (esi) m/z=449 (96), 451 (100).

Workup

  1. temperatureat reflux for 3 hours

Sources & evidence

ORD record
ord-06499f55ce514356b33c3d2972b21ff5
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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