Reserpine → N-{4-[7-Amino-3-(4-piperidyl)-1H-pyrazolo[4,3-d]pyrimidin-1-yl]-2-methoxyphenyl}-N-phenylurea

HRID 1171027Notes

Reaction equation

HRID 1171027 reaction equation
[NH2:1][C:2]1[C:3]2[N:10]([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([O:18][CH3:19])[CH:12]=3)[N:9]=[C:8]([CH:20]3[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[C:33]1(N=C=O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.NC1C2N(C3C=CC([NH:58][C:59](C4N(C)C5C(C=4)=CC=CC=5)=[O:60])=C(OC)C=3)N=C(C3CCNCC3)C=2N=CN=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>[NH2:1][C:2]1[C:3]2[N:10]([C:11]3[CH:16]=[CH:15][C:14]([N:17]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:59]([NH2:58])=[O:60])=[C:13]([O:18][CH3:19])[CH:12]=3)[N:9]=[C:8]([CH:20]3[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 5770ReserpineHCID 7672Phenyl isocyanateHCID 10006025N2-{4-[7-amino-3-(4-piperidyl)-1H-pyrazolo[4,3-d]pyrimidin-1-yl]-2-methoxyphenyl}-1-methyl-1H-2-indolecarboxamideHCID 68515091HCID 68515091, compound

Product 1

HCID 10027176N-{4-[7-Amino-3-(4-piperidyl)-1H-pyrazolo[4,3-d]pyrimidin-1-yl]-2-methoxyphenyl}-N-phenylurea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared from tert-Butyl 4-[7-amino-1-(4-amino-3-methoxyphenyl)-1H-pyrazolo[4,3-d]pyrimidin-3-yl]-1-piperidinecarboxylate and phenyl isocyanate 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 9.40 (s, 1H), 8.44 (s, 1H), 8.33 (d, 1H), 8.23 (s, 1H), 7.47 (d, 2H), 7.31 (m, 2H), 7.19 (s, 1H), 7.06 (m, 1H), 7.00 (m, 1H), 6.5 (bs, 2H), 3.95 (s, 3H), 3-3.2 (m, 3H), 2.71 (m, 2H), 1.9-2.0 (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 13.02 min; MS: MH+ 459.1, M−H+ 457.2

Sources & evidence

ORD record
ord-3fd3bd5d651b4642822291aa75b50e91
Source dataset
uspto-grants-2010_11
Patent number
US07829570B2

Reaction notes

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