Benzylamine → HCID 66558332, compound

HRID 1530503Notes

Reaction equation

HRID 1530503 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](O)=[O:32])=[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.[CH2:65]([NH2:72])[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1>CN(C=O)C>[CH2:65]([NH:72][C:31](=[O:32])[CH2:30][C:27]1[CH:28]=[CH:29][C:22]2[O:21][CH2:20][CH2:19][N:18]3[CH:17]=[C:16]([C:15]4[N:11]([CH:8]([CH3:9])[CH3:10])[N:12]=[CH:13][N:14]=4)[N:25]=[C:24]3[C:23]=2[CH:26]=1)[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 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 66558332HCID 66558332, compoundYield 84%

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 (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 benzylamine (27 mg, 0.25 mmol) in DMF (0.2 mL) and the resulting mixture stirred at RT for 3 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% tMeOH in DCM) affording 120 as a white solid (78 mg, 84%). LCMS: RT 3.94 min [M+H]+ 443.3. 1H NMR (CDCl3, 400 MHz): δ 8.38 (1H, d, J=2.31 Hz), 7.91 (1H, s), 7.75 (1H, s), 7.27-7.19 (6H, m), 7.04 (1H, d, J=8.36 Hz), 5.89-5.88 (1H, m), 5.79 (1H, s), 4.46-4.43 (6H, m), 3.68 (2H, s), 1.59 (6H, d, J=6.62 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% tMeOH in DCM)

Sources & evidence

ORD record
ord-8e8b9718f7244757bb5a8d83156a3623
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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