Ethyl isocyanatoacetate → HCID 69515578, compound

HRID 1353453Notes

Reaction equation

HRID 1353453 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[CH:7][C:8]([NH2:12])=[N:9]2)=[CH:4][CH:3]=1.[CH2:19]([O:21][C:22](=[O:27])[CH2:23][N:24]=[C:25]=[O:26])[CH3:20].C(N(C(C)C)CC)(C)C>>[CH2:19]([O:21][C:22](=[O:27])[CH2:23][NH:24][C:25]([N:16]1[CH2:17][CH2:18][N:13]([C:6]2[C:5]3[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]=[C:8]([NH2:12])[CH:7]=2)[CH2:14][CH2:15]1)=[O:26])[CH3:20]

Participants

4

Reactant 3

HCID 76283Ethyl isocyanatoacetateHCID 81531DiisopropylethylamineHCID 211017487-Chloro-4-(1-piperazinyl)-2-quinolinamine

Product 1

HCID 69515578HCID 69515578, compound

Procedure

As described example 159, 7-chloro-4-(1-piperazinyl)-2-quinolinamine (1.5 g, 5.7 mmol), isocyanato-acetic acid-ethy ester (0.7 mL, 6.3 mmol) and diisopropylethyl amine (1.5 mL, 8.6 mmol) are reacted to give [[[4-(2-amino-7-chloro-4-quinolinyl)-1-piperazinyl]carbonyl]amino]-acetic acid-ethyl ester the product as a white solid (990 mg, 40%). A mixture of the ester (990 mg), LiOH.H2O (1 g) in THF-H2O (5:1, 45 mL) was stirred at rt for 3 h, then acidified with 1.0 N HC (aq.) to pH to 4–5. After the removal of THF in vacuo, crude product precipitated. 760 mg (76%) of the acid was obtained after drying under vacuum for 3 h. LC-MS: 363 (M++1).

Workup

  1. customare reacted

Sources & evidence

ORD record
ord-93ddd96bc50649e4859d4317a4d42284
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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