Triethylamine → HCID 68759903, compound

HRID 79581Notes

Reaction equation

HRID 79581 reaction equation
[C:1]([O:5][C:6]([N:8]([CH:21]([CH3:23])[CH3:22])[CH2:9][C@H:10]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[C:11](O)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C(N=C=NCCCN(C)C)C.C1C=CC2N(O)N=NC=2C=1.O.C(N(CC)CC)C.[F:54][C:55]1[CH:60]=[CH:59][C:58]([C:61]2[C:62]([N:70]3[CH2:75][CH2:74][NH:73][CH2:72][CH2:71]3)=[C:63]3[CH:69]=[CH:68][NH:67][C:64]3=[N:65][CH:66]=2)=[CH:57][CH:56]=1>C(Cl)Cl>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C@H:10]([C:11]([N:73]2[CH2:74][CH2:75][N:70]([C:62]3[C:61]([C:58]4[CH:59]=[CH:60][C:55]([F:54])=[CH:56][CH:57]=4)=[CH:66][N:65]=[C:64]4[NH:67][CH:68]=[CH:69][C:63]=34)[CH2:71][CH2:72]2)=[O:12])[CH2:9][N:8]([CH:21]([CH3:23])[CH3:22])[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:15][CH:16]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59564929(2S)-3-[tert-butoxycarbonyl(isopropyl)amino]-2-(4-chlorophenyl)propanoic acidHCID 68762053HCID 68762053, compound

Product 1

HCID 68759903HCID 68759903, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(S)-3-(tert-Butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)propanoic acid (87 mg, 0.25 mmol, see Example H), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (65 mg, 0.34 mmol), HOBt-H2O (52 mg, 0.34 mmol) and triethylamine (51 mg, 0.51 mmol) were added to 5-(4-fluorophenyl)-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine (50 mg, 0.17 mmol) in DCM (10 mL). The reaction was stirred for 18 hours. The reaction was then diluted with DCM (50 mL) and washed with 1N HCl, 10% K2CO3 and brine. After drying with MgSO4 and concentration, the resulting residue was purified by chromatography (SP4, 12+M, water/ACN 80/20→0/100, 20CV) to yield (S)-tert-butyl 2-(4-chlorophenyl)-3-(4-(5-(4-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-oxopropyl(isopropyl)carbamate (42 mg, 40% yield) as a solid.

Workup

  1. washwashed with 1N HCl, 10% K2CO3 and brine
  2. dry with materialAfter drying with MgSO4 and concentration
  3. customthe resulting residue was purified by chromatography (SP4, 12+M, water/ACN 80/20→0/100, 20CV)

Sources & evidence

ORD record
ord-41bb995fb10f4bfb8bce7c67b16d79b8
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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