Toluene → HCID 49779585, compound

HRID 449342Notes

Reaction equation

HRID 449342 reaction equation
[C:1](Cl)(Cl)=[O:2].C1(C)C=CC=CC=1.[Cl:12][C:13]1[C:14]([F:20])=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16].C(N(CC)CC)C.Cl.[CH3:29][N:30]1[CH2:35][CH2:34][N:33]([C:36]2[CH:41]=[C:40]([C:42]3[CH:51]=[C:50]4[C:45]([CH2:46][CH2:47][NH:48][CH2:49]4)=[CH:44][CH:43]=3)[N:39]=[C:38]([NH2:52])[N:37]=2)[CH2:32][CH2:31]1>C1COCC1.C(#N)C>[NH2:52][C:38]1[N:39]=[C:40]([C:42]2[CH:51]=[C:50]3[C:45]([CH2:46][CH2:47][N:48]([C:1]([NH:16][C:15]4[CH:17]=[CH:18][CH:19]=[C:13]([Cl:12])[C:14]=4[F:20])=[O:2])[CH2:49]3)=[CH:44][CH:43]=2)[CH:41]=[C:36]([N:33]2[CH2:32][CH2:31][N:30]([CH3:29])[CH2:35][CH2:34]2)[N:37]=1

Participants

8

Reactant 5

HCID 1140TolueneHCID 6371PhosgeneHCID 8471Triethylamine2×HCID 750143-Chloro-2-fluoroanilineHCID 675414894-(4-methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine HCl salt

Product 1

HCID 49779585HCID 49779585, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 20% phosgene in toluene (phosgene:toluene=1:4, 54.9 uL, 0.104 mmol) was added a solution of 3-chloro-2-fluoroaniline (6.5 mg, 0.045 mmol) (Aldrich, Cat. #530174) and triethylamine (19.3 uL, 0.138 mmol) in THF (0.4 mL). The resulting mixture was stirred at r.t. for 2 h., and concentrated. To the residue was added a solution of 4-(4-methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine HCl salt (15 mg, 0.034 mmol) and triethylamine (19.3 uL, 0.138 mmol) in acetonitrile (0.4 mL). The reaction mixture was stirred at r.t. for 30 min The mixture was purified by RP-LCMS (pH=10) to afford the desired product. Analytic LCMS (M+H)+: m/z=496.1/498.1.

Workup

  1. concentrationconcentrated
  2. stirringThe reaction mixture was stirred at r.t. for 30 min The mixture
  3. customwas purified by RP-LCMS (pH=10)

Sources & evidence

ORD record
ord-e910d042098d4e8d815c2817a71fe541
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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