Diethylamine → HCID 71599636, compound

HRID 1507685Notes

Reaction equation

HRID 1507685 reaction equation
[CH2:1]([O:8][C:9]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([C:22](O)=[O:23])[N:11]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[C:10]=1[C:33]([OH:35])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[N:38]([CH:42]([CH3:44])C)[CH:39]([CH3:41])C.CN(C(ON1N=N[C:55]2C=[CH:57][CH:58]=[N:59][C:54]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(NCC)C>CN(C=O)C>[CH2:15]([O:14][C:13]1[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:10]([C:33]([N:59]([CH2:54][CH3:55])[CH2:58][CH3:57])=[O:35])[N:11]([C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)[C:12]=1[C:22]([N:38]([CH2:39][CH3:41])[CH2:42][CH3:44])=[O:23])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89610614HCID 89610614, compound

Product 1

HCID 71599636HCID 71599636, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bis(benzyloxy)-1-(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxylic acid (2) (400 mg, 0.85 mmol) and DIPEA (386 μL, 2.11 mmol) in DMF (4 mL) was added HATU (803 mg, 2.11 mmol) followed by diethylamine (219 μL, 2.11 mmol). The reaction mixture was stirred at RT for 1 h and then partitioned between Et2O (50 mL) and sat. NaOAc (aq.) (30 mL). The organic phase was washed succesively with sat. NaOAc (aq.) (20 mL), sat. NaHCO3 (aq.) (20 mL) and brine (2×20 mL), dried (MgSO4), filtered and concentrated in vacuo to afford the crude product. The residue was purified by silica gel chromatography (12 g, 30% EtOAc/isohexane) to afford 3,4-bis(benzyloxy)-N2,N2,N5,N5-tetraethyl-1-(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxamide (UL1-046) (201 mg, 41%) as a yellow solid: m/z 584 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 7.47-7.22 (m, 10H), 7.09-6.99 (m, 2H), 6.94-6.76 (m, 2H), 4.97 (s, 4H), 3.74 (s, 3H), 3.29-3.03 (m, 8H), 0.98-0.71 (m, 12H).

Workup

  1. custompartitioned between Et2O (50 mL) and sat. NaOAc (aq.) (30 mL)
  2. washThe organic phase was washed succesively with sat. NaOAc (aq.) (20 mL), sat. NaHCO3 (aq.) (20 mL) and brine (2×20 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford the crude product
  7. customThe residue was purified by silica gel chromatography (12 g, 30% EtOAc/isohexane)

Sources & evidence

ORD record
ord-b1c4ce8a0dea4af185b5557a06cded0b
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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