Triethylamine → HCID 67006204, compound

HRID 564536Notes

Reaction equation

HRID 564536 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:32][CH3:33])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=3)[C:26](O)=[O:27])=[O:22])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].[Br:34][C:35]1[CH:36]=[C:37]([CH2:42]N)[CH:38]=[C:39]([CH3:41])[CH:40]=1.C[N:45](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>C(Cl)Cl>[Br:34][C:35]1[CH:40]=[C:39]([CH2:41][N:20]([CH2:19][C:10]2[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]3[CH:5]=[N:4][N:3]([CH2:1][CH3:2])[C:7]3=[N:8][C:9]=2[CH2:32][CH3:33])[C:21]([C:23]2[CH:31]=[CH:30][CH:29]=[C:25]([C:26]([NH2:45])=[O:27])[CH:24]=2)=[O:22])[CH:38]=[C:37]([CH3:42])[CH:36]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 53414442HCID 53414442, compoundHCID 578132773-[({[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic Acid

Product 1

HCID 67006204HCID 67006204, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic acid (1000 mg, 2.05 mmol), [(3-bromo-5-methylphenyl)methyl]amine (605 mg, 2.25 mmol), HBTU (932 mg, 2.45 mmol) and Et3N (0.57 mL, 4.10 mmol) in DCM was stirred at room temperature overnight. The reaction was quenched with saturated NaHCO3 and extracted with DCM twice. The combined organic layers were then washed with water followed by a brine wash. The organic layer was then concentrated under vacuum to give a crude residue. It was then purified with CombiFlash chromatography, eluting with 0 to 10% methanol in DCM to obtain N-[(3-bromo-5-methylphenyl)methyl]-N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1,3-benzenedicarboxamide as an oil (652 mg, 50%). LC-MS m/z 634 (M+H)+.

Workup

  1. customThe reaction was quenched with saturated NaHCO3
  2. extractionextracted with DCM twice
  3. washThe combined organic layers were then washed with water
  4. washwash
  5. concentrationThe organic layer was then concentrated under vacuum
  6. customto give a crude residue
  7. customIt was then purified with CombiFlash chromatography
  8. washeluting with 0 to 10% methanol in DCM

Sources & evidence

ORD record
ord-9c1300161a5a420bb5ffd7eca7955562
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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