Tert-Butylamine → HCID 68163259, compound

HRID 521595Notes

Reaction equation

HRID 521595 reaction equation
C([NH:5][CH2:6][CH2:7][N:8]1[C:16]([CH2:17][C:18]2[C:27]([I:28])=[CH:26][C:21]3[O:22][CH2:23][CH2:24][O:25][C:20]=3[CH:19]=2)=[N:15][C:14]2[C:9]1=[N:10][C:11]([F:30])=[N:12][C:13]=2[NH2:29])(C)(C)C.[C:31](N)([CH3:34])([CH3:33])[CH3:32]>CN(C=O)C>[F:30][C:11]1[N:10]=[C:9]2[C:14]([N:15]=[C:16]([CH2:17][C:18]3[C:27]([I:28])=[CH:26][C:21]4[O:22][CH2:23][CH2:24][O:25][C:20]=4[CH:19]=3)[N:8]2[CH2:7][CH2:6][NH:5][CH2:32][CH:31]([CH3:34])[CH3:33])=[C:13]([NH2:29])[N:12]=1

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 68163116HCID 68163116, compound

Product 1

HCID 68163259HCID 68163259, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9-(2-(tert-butylamino)ethyl)-2-fluoro-8-((7-iodo-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methyl)-9H-purin-6-amine [DZ4-84]. S10-6 (8 mg, 0.0149 mmol) and tert-butylamine (109 mg, 157 μl) in DMF (0.5 mL) was stirred overnight at rt. Solvent was removed under reduced pressure and the resulting residue was purified by preparatory TLC (hexane:CH2Cl2:EtOAc:MeOH—NH3 (7N), 7:2:1:0.5) to give 6 mg (77%) of DZ4-84. 1H NMR (500 MHz, CDCl3) δ 7.36 (s, 1H), 6.55 (s, 1H), 5.86 (br s, 2H), 4.29 (s, 2H), 4.17-4.23 (m, 4H), 4.04 (t, J=6.4 Hz, 2H), 2.85 (t, J=6.4 Hz, 2H), 0.99 (s, 9H); MS (ESI) m/z 527.1 [M+H]+.

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe resulting residue was purified by preparatory TLC (hexane:CH2Cl2:EtOAc:MeOH—NH3 (7N), 7:2:1:0.5)
  3. customto give 6 mg (77%) of DZ4-84

Sources & evidence

ORD record
ord-d77a79d7abb846acb4a1314305bec2e6
Source dataset
uspto-grants-2016_05
Patent number
US09328114B2

Reaction notes

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