Triethylamine → HCID 86713606, compound

HRID 524089Notes

Reaction equation

HRID 524089 reaction equation
[CH3:1][C:2]1[C:3]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[N:4][C:5]([NH:8][C:9]2[CH:24]=[CH:23][C:12]([C:13]([NH:15][CH:16]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]3)=[O:14])=[CH:11][C:10]=2[N+:25]([O-:27])=[O:26])=[N:6][CH:7]=1.[N:34]([C:37]1[CH:44]=[CH:43][C:40]([C:41]#[N:42])=[CH:39][CH:38]=1)=[C:35]=[O:36].C(N(CC)CC)C>C(Cl)Cl>[C:41]([C:40]1[CH:39]=[CH:38][C:37]([NH:34][C:35]([N:31]2[CH2:32][CH2:33][N:28]([C:3]3[C:2]([CH3:1])=[CH:7][N:6]=[C:5]([NH:8][C:9]4[CH:24]=[CH:23][C:12]([C:13](=[O:14])[NH:15][CH:16]5[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]5)=[CH:11][C:10]=4[N+:25]([O-:27])=[O:26])[N:4]=3)[CH2:29][CH2:30]2)=[O:36])=[CH:44][CH:43]=1)#[N:42]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1703804-Cyanophenyl isocyanateHCID 86713607HCID 86713607, compound

Product 1

HCID 86713606HCID 86713606, compoundYield 222%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 4-((5-methyl-4-(piperazin-1-yl)pyrimidin-2-yl)amino)-N-(1-methylpiperidin-4-yl)-3-nitrobenzamide (0.073 mmol) in DCM (1.5 mL) was added 4-isocyanatobenzonitrile (23 mg, 0.16 mmol) and triethylamine (0.055 mL, 0.39 mmol) and the mixture was stirred at 23° C. for 16 h. reaction. The crude reaction mixture was filtered and washed with minimal volume of DCM and then hexanes to give the title compound (97 mg, 100%). MS (ES+) C30H34N10O4 requires: 598. found: 599 [M+H]+.

Workup

  1. customreaction
  2. customThe crude reaction mixture
  3. filtrationwas filtered
  4. washwashed with minimal volume of DCM

Sources & evidence

ORD record
ord-6d065b4ba7d24ed88954f2622ea1eda3
Source dataset
uspto-grants-2016_05
Patent number
US09340514B2

Reaction notes

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