Reserpine → N2-{4-[7-Amino-3-(4-piperidyl)-1H-pyrazolo[4,3-d]pyrimidin-1-yl]phenyl}-1-methyl-1H-2-indolecarboxamide

HRID 1171032Notes

Reaction equation

HRID 1171032 reaction equation
NC1C2N(C3C=CC(N)=CC=3)N=C(C3CCN(C(OC(C)(C)C)=O)CC3)C=2N=CN=1.CN1C2C(=CC=CC=2)C=C1C(Cl)=O.[NH2:44][C:45]1[C:46]2[N:53]([C:54]3[CH:59]=[CH:58][C:57]([NH:60][C:61]([C:63]4[N:64]([CH3:72])[C:65]5[C:70]([CH:71]=4)=[CH:69][CH:68]=[CH:67][CH:66]=5)=[O:62])=[C:56](OC)[CH:55]=3)[N:52]=[C:51]([CH:75]3[CH2:80][CH2:79][NH:78][CH2:77][CH2:76]3)[C:47]=2[N:48]=[CH:49][N:50]=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>[NH2:44][C:45]1[C:46]2[N:53]([C:54]3[CH:55]=[CH:56][C:57]([NH:60][C:61]([C:63]4[N:64]([CH3:72])[C:65]5[C:70]([CH:71]=4)=[CH:69][CH:68]=[CH:67][CH:66]=5)=[O:62])=[CH:58][CH:59]=3)[N:52]=[C:51]([CH:75]3[CH2:80][CH2:79][NH:78][CH2:77][CH2:76]3)[C:47]=2[N:48]=[CH:49][N:50]=1

Participants

6

Reactant 4

HCID 5770ReserpineHCID 10006025N2-{4-[7-amino-3-(4-piperidyl)-1H-pyrazolo[4,3-d]pyrimidin-1-yl]-2-methoxyphenyl}-1-methyl-1H-2-indolecarboxamideHCID 123033141-Methyl-1H-indole-2-carbonyl chlorideHCID 68518101tert-Butyl 4-[7-amino-1-(4-aminophenyl)-1H-pyrazolo[4,3-d]pyrimidine-3-yl]-1-piperidinecarboxylate

Product 1

HCID 10434694N2-{4-[7-Amino-3-(4-piperidyl)-1H-pyrazolo[4,3-d]pyrimidin-1-yl]phenyl}-1-methyl-1H-2-indolecarboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared from tert-butyl 4-[7-amino-1-(4-aminophenyl)-1H-pyrazolo[4,3-d]pyrimidine-3-yl]-1-piperidinecarboxylate and 1-methylindole carbonyl chloride in the manner described for the preparation of N2-{4-[7-amino-3-(4-piperidyl)-1H-pyrazolo[4,3-d]pyrimidin-1-yl]-2-methoxyphenyl}-1-methyl-1H-2-indolecarboxamide: 1H NMR (DMSO-d6, 400 MHz) δ 10.85 (s, 1H), 8.28 (s, 1H), 8.03 (d, 2H), 7.74 (d, 1H), 7.58 (d, 1H), 7.53 (d, 2H), 7.37 (s, 1H), 7.34 (t, 114), 7.15 (t, 1H), 6.5 (bs, 1.4H), 4.04 (s, 3H), 3.19 (m, 1H), 3.10 (m, 2H), 2.70 (m, 2H), 1.84-2.0 (m, 4H); 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 14.42 min; MS: MH+ 467.1, M−H+ 465.1

Sources & evidence

ORD record
ord-2153704369a942b9b0b5ac8d49064666
Source dataset
uspto-grants-2010_11
Patent number
US07829570B2

Reaction notes

Loading…