Aniline → HCID 66558331, compound

HRID 1530501Notes

Reaction equation

HRID 1530501 reaction equation
FC(F)(F)C(O)=O.[CH:8]([N:11]1[C:15]([C:16]2[N:25]=[C:24]3[N:18]([CH2:19][CH2:20][O:21][C:22]4[CH:29]=[CH:28][C:27]([CH2:30][C:31]([OH:33])=O)=[CH:26][C:23]=43)[CH:17]=2)=[N:14][CH:13]=[N:12]1)([CH3:10])[CH3:9].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[C:65]1([NH2:71])[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1>CN(C=O)C>[CH:8]([N:11]1[C:15]([C:16]2[N:25]=[C:24]3[C:23]4[CH:26]=[C:27]([CH2:30][C:31]([NH:71][C:65]5[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=5)=[O:33])[CH:28]=[CH:29][C:22]=4[O:21][CH2:20][CH2:19][N:18]3[CH:17]=2)=[N:14][CH:13]=[N:12]1)([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 6115AnilineHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68313159HCID 68313159, compound

Product 1

HCID 66558331HCID 66558331, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of [2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-9-yl]acetic acid trifluoroacetic acid salt from Example 120 (100 mg, 0.21 mmol), HATU (96 mg, 0.25 mmol) and NEt3 (63 mg, 0.63 mmol) in DMF (2 mL) was added a solution of phenylamine (23 mg, 0.25 mmol) in DMF (0.2 mL) and the resulting mixture stirred at RT for 16 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH. The resulting residue was purified by column chromatography (Si-PCC, gradient 0-8% MeOH in DCM) affording 119 as a white solid (51 mg, 57%). LCMS: RT 4.09 min [M+H]+ 429.3. 1H NMR (CDCl3, 400 MHz): δ 8.43 (1H, d, J=2.27 Hz), 7.91 (1H, s), 7.72 (1H, s), 7.47 (2H, d, J=8.02 Hz), 7.43 (1H, s), 7.29-7.26 (2H, m), 7.09-7.06 (2H, m), 5.86-5.85 (1H, m), 4.46-4.45 (4H, m), 3.78 (2H, s), 1.55 (6H, d, J=6.61 Hz)

Workup

  1. washwas washed with MeOH
  2. washthe product eluted with 2M NH3/MeOH
  3. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 0-8% MeOH in DCM)

Sources & evidence

ORD record
ord-dd25d7ec202341e8bec638f9b8b77203
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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