Diisopropylethylamine → HCID 69676469, compound

HRID 919641Notes

Reaction equation

HRID 919641 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([NH:7][C:8]2[C:13]([C:14]([NH2:16])=[O:15])=[CH:12][N:11]=[C:10]3[NH:17][CH:18]=[CH:19][C:9]=23)[CH2:2]1.[Cl:20][C:21]1[CH:22]=[C:23]([NH:28][CH2:29][C:30](O)=[O:31])[CH:24]=[C:25]([F:27])[CH:26]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:20][C:21]1[CH:22]=[C:23]([NH:28][CH2:29][C:30]([N:1]2[CH2:6][CH2:5][CH2:4][CH:3]([NH:7][C:8]3[C:13]([C:14]([NH2:16])=[O:15])=[CH:12][N:11]=[C:10]4[NH:17][CH:18]=[CH:19][C:9]=34)[CH2:2]2)=[O:31])[CH:24]=[C:25]([F:27])[CH:26]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67515603HCID 67515603, compoundHCID 67518186HCID 67518186, compound

Product 1

HCID 69676469HCID 69676469, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(piperidin-3-ylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (132 mg, 0.51 mmol, 1.0 eq) and 2-((3-chloro-5-fluorophenyl)amino)acetic acid (124 mg, 0.61 mmol, 1.2 eq) in DMF (3 mL) was added HBTU (387 mg, 1.02 mmol, 2.0 eq) and DIPEA (1 mL). The resulting mixture was stirred at 80° C. for 16 h and the solvent was concentrated in vacuo to afford a residue which was purified by prep-HPLC (MeOH/H2O with 0.05% TFA as mobile phase) to give afford the title compound as a light brown solid (110 mg, yield: 50%). 1H NMR (400 MHz, CD3OD) δ: 8.23 (s, 1H), 7.09-7.02 (m, 1H), 6.66-6.61 (m, 1H), 6.42-5.94 (m, 3H), 4.35-4.10 (m, 1H), 4.08-3.91 (m, 2H), 3.79-3.74 (m, 1H), 3.65-3.53 (m, 2H), 3.43-3.40 (m, 2H), 2.06-2.04 (m, 1H), 1.82-1.73 (m, 2H), 1.62-1.59 (m, 1H). ESI-MS (M+H)+: 445.15.

Workup

  1. concentrationthe solvent was concentrated in vacuo
  2. customto afford a residue which
  3. customwas purified by prep-HPLC (MeOH/H2O with 0.05% TFA as mobile phase)
  4. customto give

Sources & evidence

ORD record
ord-5283fc8ffd484884867e2f90b53a7910
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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