Acetaldehyde → N2-{4-[7-amino-3-(1-ethyl-4-piperidyl)-1H-pyrazolo[4,3-d]pyrimidin-1-yl]-2-methoxyphenyl}-1-methyl-1H-2-indolecarboxamide maleate

HRID 1171028Notes

Reaction equation

HRID 1171028 reaction equation
NC1C2N(C3C=CC(NC(C4N(C)C5C(C=4)=CC=CC=5)=O)=C(OC)C=3)N=C(C3CCNCC3)C=2N=CN=1.C(=O)C.[C:41]([OH:48])(=[O:47])/[CH:42]=[CH:43]\[C:44]([OH:46])=[O:45].[NH2:49][C:50]1[C:51]2[N:58]([C:59]3[CH:64]=[CH:63][C:62]([NH:65][C:66]([C:68]4[N:69]([CH3:77])[C:70]5[C:75]([CH:76]=4)=[CH:74][CH:73]=[CH:72][CH:71]=5)=[O:67])=[C:61]([O:78][CH3:79])[CH:60]=3)[N:57]=[C:56]([CH:80]3[CH2:85][CH2:84][N:83]([CH:86]4CCOC[CH2:87]4)[CH2:82][CH2:81]3)[C:52]=2[N:53]=[CH:54][N:55]=1.CO[C@@H]1[C@@H](C(OC)=O)[C@@H]2[C@@H](CN3[C@H](C2)C2NC4C=C(OC)C=CC=4C=2CC3)C[C@H]1OC(C1C=C(OC)C(OC)=C(OC)C=1)=O>C(#N)C>[C:41]([OH:48])(=[O:47])/[CH:42]=[CH:43]\[C:44]([OH:46])=[O:45].[NH2:49][C:50]1[C:51]2[N:58]([C:59]3[CH:64]=[CH:63][C:62]([NH:65][C:66]([C:68]4[N:69]([CH3:77])[C:70]5[C:75]([CH:76]=4)=[CH:74][CH:73]=[CH:72][CH:71]=5)=[O:67])=[C:61]([O:78][CH3:79])[CH:60]=3)[N:57]=[C:56]([CH:80]3[CH2:85][CH2:84][N:83]([CH2:86][CH3:87])[CH2:82][CH2:81]3)[C:52]=2[N:53]=[CH:54][N:55]=1

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 5770ReserpineHCID 10006025N2-{4-[7-amino-3-(4-piperidyl)-1H-pyrazolo[4,3-d]pyrimidin-1-yl]-2-methoxyphenyl}-1-methyl-1H-2-indolecarboxamideHCID 68517777N2-{4-[7-amino-3-(1-tetrahydro-2H-4-pyranyl-4-piperidyl)-1H-pyrazolo[4,3-d]pyrimidin-1-yl]-2-methoxyphenyl}-1-methyl-1H-2-indolecarboxamide maleate

Product 1

HCID 68515121N2-{4-[7-amino-3-(1-ethyl-4-piperidyl)-1H-pyrazolo[4,3-d]pyrimidin-1-yl]-2-methoxyphenyl}-1-methyl-1H-2-indolecarboxamide maleate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared from N2-{4-[7-amino-3-(4-piperidyl)-1H-pyrazolo[4,3-d]pyrimidin-1-yl]-2-methoxyphenyl}-1-methyl-1H-2-indolecarboxamide and acetaldehyde in the manner described for the preparation N2-{4-[7-amino-3-(1-tetrahydro-2H-4-pyranyl-4-piperidyl)-1H-pyrazolo[4,3-d]pyrimidin-1-yl]-2-methoxyphenyl}-1-methyl-1H-2-indolecarboxamide maleate: 1H NMR (DMSO-d6, 400 MHz) δ 9.49 (s, 1H), 9.10 (bs, 1H), 8.33 (s, 1H), 8.13 (d, 1H), 7.71 (d, 1H), 7.59 (d, 1H), 7.28-7.35 (m, 3H), 7.15 (m, 2H), 6.80 (bs, 2H), 6.01 (s, 2H), 4.04 (s, 3H), 3.94 (s, 3H), 3.62 (m, 2H), 3.38 (m, 1H), 3.16 (m, 4H), 2.26 (m, 4H), 1.27 (t, 3H); RP-HPLC (Hypersil HS C18, 5 μm, 100 A, 250×4.6 mm; 5%-100% acetonitrile-0.05 M ammonium acetate over 25 min, 1 mL/min) tr 15.77 min; MS: MH+ 525.0, M−H+ 523.0

Sources & evidence

ORD record
ord-be701998ca5c43ceaeb2197d10fce451
Source dataset
uspto-grants-2010_11
Patent number
US07829570B2

Reaction notes

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