1-Tert-butyl-4-isocyanatobenzene → HCID 67818966, compound

HRID 1024664Notes

Reaction equation

HRID 1024664 reaction equation
[CH3:1][O:2][C:3]1[CH:38]=[C:37]([O:39][CH3:40])[CH:36]=[CH:35][C:4]=1[CH2:5][NH:6][C:7]1[C:8]2[CH:15]=[CH:14][N:13]([C@H:16]3[C@@H:20]4[O:21][C:22]([CH3:25])([CH3:24])[O:23][C@@H:19]4[C@@H:18]([CH2:26][N:27]([CH:32]([CH3:34])[CH3:33])[CH2:28][CH2:29][CH2:30][NH2:31])[O:17]3)[C:9]=2[N:10]=[CH:11][N:12]=1.[C:41]([C:45]1[CH:50]=[CH:49][C:48]([N:51]=[C:52]=[O:53])=[CH:47][CH:46]=1)([CH3:44])([CH3:43])[CH3:42]>C(Cl)Cl>[C:41]([C:45]1[CH:50]=[CH:49][C:48]([NH:51][C:52]([NH:31][CH2:30][CH2:29][CH2:28][N:27]([CH2:26][C@@H:18]2[C@@H:19]3[C@@H:20]([O:21][C:22]([CH3:24])([CH3:25])[O:23]3)[C@H:16]([N:13]3[C:9]4[N:10]=[CH:11][N:12]=[C:7]([NH:6][CH2:5][C:4]5[CH:35]=[CH:36][C:37]([O:39][CH3:40])=[CH:38][C:3]=5[O:2][CH3:1])[C:8]=4[CH:15]=[CH:14]3)[O:17]2)[CH:32]([CH3:34])[CH3:33])=[O:53])=[CH:47][CH:46]=1)([CH3:44])([CH3:42])[CH3:43]

Participants

4

Reactant 2

HCID 27356951-Tert-butyl-4-isocyanatobenzeneHCID 86300750HCID 86300750, compound

Product 1

HCID 67818966HCID 67818966, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of N1-(((3aR,4R,6R,6aR)-6-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)-N1-isopropylpropane-1,3-diamine (1.11 g, 2.00 mmol, crude from step 6) in methylene chloride (40 mL) was treated dropwise with a solution of 1-tert-butyl-4-isocyanatobenzene (0.36 mL, 2.0 mmol) in methylene chloride (3.5 mL) and allowed to stir at room temperature. After 1 h, reaction was complete by HPLC. The reaction mixture was concentrated to yield a glass. The crude material was purified by flash chromatography (100 g silica gel, 2-4% 7N NH3 in CH3OH/CH2Cl2 to yield the title compound (1.07 g, 73%) as a foam: MS (ESI+) for C10H55N7O6 m/z 730.4 (M+H)+; (ESI−) for C40H55N7O6 m/z 728.5 (M−H)−; HPLC purity, 89% (ret. time, 3.78 min).

Workup

  1. customreaction
  2. concentrationThe reaction mixture was concentrated
  3. customto yield a glass
  4. customThe crude material was purified by flash chromatography (100 g silica gel, 2-4% 7N NH3 in CH3OH/CH2Cl2

Sources & evidence

ORD record
ord-6f9a2726e56f4df786b0f85774ac263d
Source dataset
uspto-grants-2014_05
Patent number
US08722877B2

Reaction notes

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