Bis(trimethylsilyl)carbodiimide → HCID 58980958, compound

HRID 1181813Notes

Reaction equation

HRID 1181813 reaction equation
[NH:1]([C:3]1[N:8](CC(C)C)C(=O)N(C)C(=O)C=1)N.ClC1C=C2C(=CC=1)NC=C2C=O.C(C1C=C(C=O)N(C)C=1)(=O)C.[C:39]([C:42]1[CH:43]=[C:44]([C:48]2[N:49]([CH2:64][C:65]3[C:73]4[C:68](=[CH:69][CH:70]=[C:71]([Cl:74])[CH:72]=4)[NH:67][CH:66]=3)[N:50]=[C:51]3[C:56]=2[C:55](=[O:57])[N:54]([CH3:58])[C:53](=[O:59])[N:52]3[CH2:60][CH:61]([CH3:63])[CH3:62])[N:45]([CH3:47])[CH:46]=1)(=O)[CH3:40].C[Si](N=C=N[Si](C)(C)C)(C)C>ClCCl.Cl[Ti](Cl)(Cl)Cl>[Cl:74][C:71]1[CH:72]=[C:73]2[C:68](=[CH:69][CH:70]=1)[NH:67][CH:66]=[C:65]2[CH2:64][N:49]1[C:48]([C:44]2[N:45]([CH3:47])[CH:46]=[C:42]([C:39](=[N:8][C:3]#[N:1])[CH3:40])[CH:43]=2)=[C:56]2[C:51]([N:52]([CH2:60][CH:61]([CH3:62])[CH3:63])[C:53](=[O:59])[N:54]([CH3:58])[C:55]2=[O:57])=[N:50]1

Participants

8

Reactant 5

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 27953745-chloro-1H-indole-3-carbaldehydeHCID 126762684-Acetyl-1-methyl-1H-pyrrole-2-carbaldehydeHCID 193560846-hydrazino-1-isobutyl-3-methyl-2,4(1H,3H)-pyrimidinedioneHCID 589811403-(4-acetyl-1-methyl-1H-pyrrol-2-yl)-2-[(5-chloro-1H-indol-3-yl)methyl]-7-isobutyl-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Product 1

HCID 58980958HCID 58980958, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

This compound was made in two steps following the procedure described above, starting with 6-hydrazino-1-isobutyl-3-methylpyrimidine-2,4(1H,3H)-dione, and condensing first 5-chloro-1H-indole-3-carbaldehyde, followed by 4-acetyl-1-methyl-1H-pyrrole-2-carbaldehyde. The isolated 3-(4-acetyl-1-methyl-1H-pyrrol-2-yl)-2-[(5-chloro-1H-indol-3-yl)methyl]-7-isobutyl-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione was treated with a cold solution of bis(trimethylsilyl)carbodiimide and TiCl4 at 0° C. in anhydrous dichloromethane. The mixture was stirred at room temperature for 4 h. The crude reaction product was purified by semi-prep RPHPLC eluting with water/acetonitrile/trifluoroacetic acid mixtures. 531.2 (M+H).

Workup

  1. customThe crude reaction product
  2. customwas purified by semi-prep RPHPLC
  3. washeluting with water/acetonitrile/trifluoroacetic acid mixtures

Sources & evidence

ORD record
ord-8f1b9733a04f4c7b8720531dbf7cfb38
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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