Triethylamine → HCID 86645777, compound

HRID 449367Notes

Reaction equation

HRID 449367 reaction equation
[N:1]([C@@H:4]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])=[C:2]=[O:3].Cl.[CH3:17][N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[C:28]([C:30]3[CH:39]=[C:38]4[C:33]([CH2:34][CH2:35][NH:36][CH2:37]4)=[CH:32][CH:31]=3)[N:27]=[C:26]([NH2:40])[N:25]=2)[CH2:20][CH2:19]1.C(N(CC)CC)C>C(#N)C>[NH2:40][C:26]1[N:27]=[C:28]([C:30]2[CH:39]=[C:38]3[C:33]([CH2:34][CH2:35][N:36]([C:2]([NH:1][C@@H:4]([CH2:9][C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[C:5]([O:7][CH3:8])=[O:6])=[O:3])[CH2:37]3)=[CH:32][CH:31]=2)[CH:29]=[C:24]([N:21]2[CH2:20][CH2:19][N:18]([CH3:17])[CH2:23][CH2:22]2)[N:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1514293Methyl N-(oxomethylidene)phenylalaninateHCID 675414894-(4-methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine HCl salt

Product 1

HCID 86645777HCID 86645777, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl (2S)-2-isocyanato-3-phenylpropanoate (12.5 mg, 0.0609 mmol) (Aldrich, Cat. #409731) was added to a mixture of 4-(4-methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine HCl salt (25.0 mg, 0.0576 mmol) and triethylamine (32 uL, 0.23 mmol) in acetonitrile (1.0 mL). After 30 min., the mixture was concentrated, and purified by flash chromatography on a silica gel column with MeOH in dichloromethylene (0-5%) to afford the desired product (30 mg, 98%). Analytic LCMS (M+H)+: m/z=530.2.

Workup

  1. concentrationthe mixture was concentrated
  2. custompurified by flash chromatography on a silica gel column with MeOH in dichloromethylene (0-5%)

Sources & evidence

ORD record
ord-78a049c4fd4c460aaaf9111c0b8b372a
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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