Diisopropylethylamine → HCID 59605923, compound

HRID 1946138Notes

Reaction equation

HRID 1946138 reaction equation
[CH3:1][C:2]1([CH3:36])[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[CH2:8][C:9]1[N:10]([CH3:35])[C:11]2[C:16]([N:17]=1)=[C:15]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[N:14]=[C:13]([N:24]1[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[N:26]=[C:25]1[CH2:33][CH3:34])[N:12]=2.[C:37](O)(=[O:41])[C@H:38]([CH3:40])[OH:39].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:33]([C:25]1[N:24]([C:13]2[N:12]=[C:11]3[C:16]([N:17]=[C:9]([CH2:8][N:3]4[CH2:4][CH2:5][N:6]([C:37](=[O:41])[C@@H:38]([OH:39])[CH3:40])[CH2:7][C:2]4([CH3:1])[CH3:36])[N:10]3[CH3:35])=[C:15]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[N:14]=2)[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[N:26]=1)[CH3:34]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 107689L-Lactic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67492830HCID 67492830, compound

Product 1

HCID 59605923HCID 59605923, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 8-(2,2-dimethylpiperazin-1-ylmethyl)-2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine (100 mg, 0.20 mmol), L-Lactic acid (17 μL, 0.22 mmol), HATU (85 mg, 0.22 mmol) and DIPEA (40 μL, 0.23 mmol) in DCM (2 mL) was allowed to stir at r.t. 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, MeOH:DCM, 2%) affording 723 as a white solid (27 mg, 29%). LCMS (method I): RT 2.90 min, [M+H]+ 562.3. 1H NMR (CDCl3, 400 MHz): δ 8.02-8.00 (1 H, m), 7.78-7.74 (1 H, m), 7.35-7.25 (2 H, s), 4.46-4.43 (1 H, m), 4.34 (4 H, brd s), 4.06-3.94 (1 H, m), 3.91 (3 H, s), 3.86 (4 H, t, J=4.68 Hz), 3.76-3.75 (2 H, m), 3.50-3.48 (1 H, m), 3.37-3.35 (3 H, m), 3.24-3.22 (1 H, m), 2.59-2.53 (2 H, m), 1.45 (3 H, t, J=7.48 Hz), 1.34-1.30 (4 H, m), 1.26-1.15 (5 H, m)

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, MeOH:DCM, 2%)

Sources & evidence

ORD record
ord-fbd8d4bf9ec54064919a1b4a0c75420f
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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