Triethylamine → HCID 59606151, compound

HRID 1923320Notes

Reaction equation

HRID 1923320 reaction equation
[CH2:1]([C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[C:13]([C:18](O)=[O:19])[N:14]3[CH3:17])=[C:10]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[N:9]=2)[C:6]2[CH:27]=[CH:28][CH:29]=[CH:30][C:5]=2[N:4]=1)[CH3:2].[CH3:31][S:32]([N:35]1[CH2:40][CH2:39][NH:38][C:37]([CH3:42])([CH3:41])[CH2:36]1)(=[O:34])=[O:33].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>CN(C=O)C>[CH3:41][C:37]1([CH3:42])[CH2:36][N:35]([S:32]([CH3:31])(=[O:33])=[O:34])[CH2:40][CH2:39][N:38]1[C:18]([C:13]1[N:14]([CH3:17])[C:15]2[C:11]([N:12]=1)=[C:10]([N:21]1[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1)[N:9]=[C:8]([N:7]1[C:6]3[CH:27]=[CH:28][CH:29]=[CH:30][C:5]=3[N:4]=[C:3]1[CH2:1][CH3:2])[N:16]=2)=[O:19]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 198151421-Methanesulfonyl-3,3-dimethylpiperazineHCID 596053252-(2-ethyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purine-8-carboxylic acid

Product 1

HCID 59606151HCID 59606151, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carboxylic acid (117 mg, 0.26 mmol), 1-methanesulfonyl-3,3-dimethylpiperazine (51 mg, 0.26 mmol) and HATU (100 mg, 0.26 mmol) in DMF (1 mL) was added NEt3 (720 μL, 5.18 mmol). The resulting mixture was allowed to stir at r.t. for 16 h then partitioned between EtOAc and H2O. The organic phase was dried (MgSO4) and concentrated in vacuo and the resulting residue was purified by column chromatography (Si—PCC, MeOH:EtOAc, 0-5%). The resulting solid was recrystallised from EtOAc and Et2O affording 715 (50 mg, 33%). LCMS (method I): RT 3.68 min, [M+H]+ 582.2. 1H NMR (CDCl3, 400 MHz): δ 8.03-8.03 (1 H, m), 7.76-7.75 (1 H, m), 7.31-7.27 (2 H, m), 4.35 (4 H, brd s), 4.03 (2 H, t, J=5.39 Hz), 3.95 (3 H, s), 3.87 (4 H, t, J=4.70 Hz), 3.50 (2 H, t, J=5.40 Hz), 3.37 (2 H, q, J=7.47 Hz), 3.31 (2 H, s), 2.90 (3 H, s), 1.68 (6 H, s), 1.45 (3 H, t, J=7.47 Hz)

Workup

  1. customthen partitioned between EtOAc and H2O
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customthe resulting residue was purified by column chromatography (Si—PCC, MeOH:EtOAc, 0-5%)
  5. customThe resulting solid was recrystallised from EtOAc and Et2O affording 715 (50 mg, 33%)
  6. customRT 3.68 min, [M+H]+ 582.2

Sources & evidence

ORD record
ord-466ae7fdfd024683a79ad1cce249d708
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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