O-Methylhydroxylamine hydrochloride → HCID 58980992, compound

HRID 1181817Notes

Reaction equation

HRID 1181817 reaction equation
N(C1N(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].Cl.[CH3:76][O:77][NH2:78]>>[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:78]/[O:77][CH3:76])/[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

6

Reactant 5

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 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 58980992HCID 58980992, compound

Procedure

This compound was made 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. To 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 added 4 equivalents of methoxyamine hydrochloride, triethylamie and heated at 80° C. in N,N′dimethylacetamide for 4 h. The mixture was stirred at room temperature for 4 h. The crude reaction product was purified by semi-prep RPHPLC eluting with water/acetonitrile/trfluoroacetic acid mixtures. 536.2 (M+H).

Workup

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

Sources & evidence

ORD record
ord-59c4bf4616584582a3a2caa3a4351445
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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