Hydrochloric Acid → HCID 46701391, compound

HRID 2090319Notes

Reaction equation

HRID 2090319 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][C:12]([N:18]4[CH2:23][CH2:22][N:21]([C:24](OC(C)(C)C)=[O:25])[CH2:20][CH2:19]4)=[CH:13][CH:14]=3)[CH2:9]2)[CH:5]=[C:4]([N:31]2[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]2)[N:3]=1.[ClH:38].C([N:41]([CH2:44][CH3:45])CC)C>O1CCOCC1.C(#N)C.CO>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][C:12]([N:18]4[CH2:23][CH2:22][N:21]([C:24]([NH:41][C:44]5[CH:45]=[CH:12][C:11]([Cl:38])=[CH:10][CH:9]=5)=[O:25])[CH2:20][CH2:19]4)=[CH:13][CH:14]=3)[CH2:9]2)[CH:5]=[C:4]([N:31]2[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]2)[N:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 59402300HCID 59402300, compound

Product 1

HCID 46701391HCID 46701391, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 4-{2-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-1,2,3,4-tetrahydroisoquinolin-7-yl}piperazine-1-carboxylate (16 mg, 0.031 mmol) was treated with 4M HCl in dioxane (0.5 mL) at r.t. for 1 h. The reaction mixture was concentrated to dryness. 1-Chloro-4-isocyanatobenzene (5.0 uL, 0.041 mmol, Aldrich, Cat. No. 152277) was added to a mixture of above residue and triethylamine (22 uL, 0.16 mmol) in acetonitrile (1.0 mL). After stirring at r.t. for 2 h., the reaction mixture was diluted with MeOH and purified by RP-HPLC (pH=10 system) to afford the desired compound. LCMS(M+H)+: m/z=562.3.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. custompurified by RP-HPLC (pH=10 system)

Sources & evidence

ORD record
ord-e21dd7e374674168b6f62bda6fad7e16
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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