Triethylamine → HCID 118207803, compound

HRID 2205633Notes

Reaction equation

HRID 2205633 reaction equation
[NH2:1][C@H:2]([C:4]1[N:9]=[C:8]2[CH:10]=[CH:11][N:12]([CH3:13])[C:7]2=[CH:6][C:5]=1[N:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)[CH3:3].Cl[C:28]1[C:33]([C:34]#[N:35])=[C:32]([CH2:36][CH3:37])[N:31]=[C:30]([S:38][CH3:39])[N:29]=1.CCN(CC)CC>C1COCC1.CCOC(C)=O>[C:34]([C:33]1[C:28]([NH:1][C@H:2]([C:4]2[N:9]=[C:8]3[CH:10]=[CH:11][N:12]([CH3:13])[C:7]3=[CH:6][C:5]=2[N:14]2[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:18][CH2:19]2)[CH3:3])=[N:29][C:30]([S:38][CH3:39])=[N:31][C:32]=1[CH2:36][CH3:37])#[N:35]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 118207754HCID 118207754, compoundHCID 118207781HCID 118207781, compound

Product 1

HCID 118207803HCID 118207803, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a 20 mL vial were added (S)-tert-butyl 4-(5-(1-aminoethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)piperazine-1-carboxylate (63 mg, 0.175 mmol) in THF (5 mL), 4-chloro-6-ethyl-2-(methylthio)pyrimidine-5-carbonitrile (37.5 mg, 0.175 mmol) and Et3N (0.027 mL, 0.193 mmol). The resulting yellow solution was heated to 60° C. and stirred overnight. The next day LCMS indicated the reaction was mostly complete. The reaction mixture was diluted with EtOAc and washed with saturated aqueous NH4Cl (3×). The combined organic layers were dried over MgSO4, filtered, and concentrated. The product was purified by column chromatography (ISCO 12 g, 30-100% EtOAc/hexane gradient) to give the title compound as a yellow solid. ESI-MS m/z [M+H]+ calc'd for C27H36N8O2S, 537. found 537.

Workup

  1. washwashed with saturated aqueous NH4Cl (3×)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was purified by column chromatography (ISCO 12 g, 30-100% EtOAc/hexane gradient)

Sources & evidence

ORD record
ord-d6c257299bac40e98d545108ff100bb3
Source dataset
uspto-grants-2016_06
Patent number
US09371321B2

Reaction notes

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