Chloroacetone → N-(3-(benzyloxy)-5-bromopyrazin-2-yl)-4-methylthiazol-2-amine

HRID 1426101Notes

Reaction equation

HRID 1426101 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:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:21][C:22](=O)[CH3:23].C(N(CC)CC)C>C(O)C>[CH2:1]([O:8][C:9]1[C:10]([NH:16][C:17]2[S:18][CH:21]=[C:22]([CH3:23])[N:19]=2)=[N:11][CH:12]=[C:13]([Br:15])[N:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 8471TriethylamineHCID 866396551-(3-(Benzyloxy)-5-bromopyrazin-2-yl)thiourea

Product 1

HCID 59225649N-(3-(benzyloxy)-5-bromopyrazin-2-yl)-4-methylthiazol-2-amineYield 31%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the method of Example 1, Step D, 1-(3-(benzyloxy)-5-bromopyrazin-2-yl)thiourea (952 mg, 2.81 mmol), 1-chloropropan-2-one (364 mg, 3.93 mmol) and triethylamine (0.655 mL, 4.77 mmol) were reacted in ethanol (10 mL) to provide N-(3-(benzyloxy)-5-bromopyrazin-2-yl)-4-methylthiazol-2-amine (325 mg, 31%) as a light tan powder. 1H NMR (d6-DMSO) δ 8.01 (s, 1H), 7.57 (d, 2H), 7.35-7.43 (m, 3H), 6.62 (s, 1H), 5.42 (s, 2H), 2.32 (s, 3H). Mass spectrum (apci) m/z=377 (100), 379 (97) (M+H).

Sources & evidence

ORD record
ord-72a537b79f4b40efa9bddf657049d96d
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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