Triethylamine → HCID 118214743, compound

HRID 2205603Notes

Reaction equation

HRID 2205603 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]#[N:10])=[C:4]([CH3:11])[N:3]=1.[NH2:12][C@H:13]([C:15]1[N:20]=[C:19]2[CH:21]=[CH:22][N:23]([CH3:24])[C:18]2=[CH:17][C:16]=1[N:25]1[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@@H:27]([CH3:38])[CH2:26]1)[CH3:14].C(N(CC)CC)C>CS(C)=O>[NH2:1][C:2]1[N:7]=[C:6]([NH:12][C@H:13]([C:15]2[N:20]=[C:19]3[CH:21]=[CH:22][N:23]([CH3:24])[C:18]3=[CH:17][C:16]=2[N:25]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])[C@@H:27]([CH3:38])[CH2:26]2)[CH3:14])[C:5]([C:9]#[N:10])=[C:4]([CH3:11])[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 754124462-Amino-4-chloro-6-methyl-5-pyrimidinecarbonitrileHCID 118214744HCID 118214744, compound

Product 1

HCID 118214743HCID 118214743, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
85 °C

Procedure

To a 250 mL round-bottom flask were added 2-amino-4-chloro-6-methylpyrimidine-5-carbonitrile (0.821 g, 4.87 mmol) and tert-butyl (S)-4-(5-((S)-1-aminoethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-2-methylpiperazine-1-carboxylate (1.40 g, 3.75 mmol) in DMSO (15 mL). Triethylamine (2.1 mL, 15 mmol) was added to the mixture, which was then heated to 85° C. for 2 hours. After cooling, the mixture was partitioned between saturated NaHCO3 and ethyl acetate. The aqueous layer was extracted with ethyl acetate. The organic layers were combined, dried over MgSO4, filtered, and concentrated. The crude product was purified by column chromatography (SiO2, 20-100% EtOAc/heptane gradient). The product-containing fractions were combined and then concentrated in vacuo to give the title compound as light-yellow oil (1.7 g, 90%). ESI-MS m/z [M+H]+ calc'd for C26H35N9O2, 506. found 506.

Workup

  1. temperatureAfter cooling
  2. customthe mixture was partitioned between saturated NaHCO3 and ethyl acetate
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (SiO2, 20-100% EtOAc/heptane gradient)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-830e6f4680a643039be93568a65e2b82
Source dataset
uspto-grants-2016_06
Patent number
US09371321B2

Reaction notes

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