Reserpine → tert-Butyl 4-[7-amino-1-(4-aminophenyl)-1H-pyrazolo[4,3-d]pyrimidine-3-yl]-1-piperidinecarboxylate

HRID 1171031Notes

Reaction equation

HRID 1171031 reaction equation
[NH2:1][C:2]1[C:3]2[N:10]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=3)[N:9]=[C:8]([C:20]3[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH:25]=3)[C:4]=2[N:5]=[CH:6][N:7]=1.NC1C2N(C3C=CC(N)=C(OC)C=3)N=C(C3CCN(C(OC(C)(C)C)=O)CC3)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]([NH2:17])=[CH:13][CH:12]=3)[N:9]=[C:8]([CH:20]3[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:25]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 5770ReserpineHCID 68515091HCID 68515091, compoundHCID 68519460tert-Butyl 4-[7-amino-1-(4-nitrophenyl)-1H-pyrazolo[4,3-d]pyrimidine-3-yl]-1,2,3,6-tetrahydro-1-pyridinecarboxylate

Product 1

HCID 68518101tert-Butyl 4-[7-amino-1-(4-aminophenyl)-1H-pyrazolo[4,3-d]pyrimidine-3-yl]-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared from tert-butyl 4-[7-amino-1-(4-nitrophenyl)-1H-pyrazolo[4,3-d]pyrimidine-3-yl]-1,2,3,6-tetrahydro-1-pyridinecarboxylate in the same manner as described for the preparation of tert-butyl 4-[7-amino-1-(4-amino-3-methoxyphenyl)-1H-pyrazolo[4,3-d]pyrimidin-3-yl]-1-piperidinecarboxylate: 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 16.07 min; MS: MH+ 410.2

Sources & evidence

ORD record
ord-2ddc6ea4a1fd463895f5036df1678af9
Source dataset
uspto-grants-2010_11
Patent number
US07829570B2

Reaction notes

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