Methanol → HCID 70855507, compound

HRID 527854Notes

Reaction equation

HRID 527854 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([S:25][C:26]1[C:34]([N:35]([CH3:37])[CH3:36])=[CH:33][C:29]3[O:30][CH2:31][O:32][C:28]=3[CH:27]=1)[N:6]2[CH2:11][CH2:12][CH2:13][N:14]1C(=O)C2C(=CC=CC=2)C1=O.O.NN.CO>C(Cl)Cl>[NH2:14][CH2:13][CH2:12][CH2:11][N:6]1[C:5]([S:25][C:26]2[C:34]([N:35]([CH3:37])[CH3:36])=[CH:33][C:29]3[O:30][CH2:31][O:32][C:28]=3[CH:27]=2)=[N:4][C:3]2[C:7]1=[N:8][CH:9]=[N:10][C:2]=2[NH2:1]

Participants

5

Reactant 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 70819565HCID 70819565, compound

Product 1

HCID 70855507HCID 70855507, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(3-(6-Amino-8-(6-(dimethylamino)benzo[d][1,3]dioxol-5-ylthio)-9H-purin-9-yl)propyl)isoindoline-1,3-dione (0.72 g, 1.38 mmol), hydrazine hydrate (2.86 g, 2.78 mL, 20.75 mmol), in CH2Cl2:MeOH (4 mL:28 mL) was stirred for 2 h at rt. The mixture was dried under reduced pressure and the residue purified by column chromatography (CH2Cl2:MeOH—NH3(7N), 20:1) to give 430 mg (80%) of the titled compound. 1H NMR (500 MHz, CDCl3): δ 8.33 (s, 1H), 6.77 (s, 1H), 6.49 (s, 1H), 5.91 (s, 2H), 5.85 (br s, 2H), 4.30 (t, J=6.9 Hz, 2H), 2.69 (s, 6H), 2.65 (t, J=6.5 Hz, 2H), 1.89-1.95 (m, 2H); 13C NMR (125 MHz, CDCl3): δ 154.5, 153.1, 151.7, 148.1, 147.2, 146.4, 144.8, 120.2, 120.1, 109.3, 109.2, 101.7, 45.3, 45.2, 40.9, 38.6, 333; HRMS (ESI) m/z [M+H]+ calcd. for C17H22N7O2S, 388.1556. found 388.1544.

Workup

  1. customThe mixture was dried under reduced pressure
  2. customthe residue purified by column chromatography (CH2Cl2:MeOH—NH3(7N), 20:1)

Sources & evidence

ORD record
ord-3eb81f7cba1b4b2196fe3b86e73dd99d
Source dataset
uspto-grants-2016_05
Patent number
US09346808B2

Reaction notes

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