1-Boc-octahydropyrrolo(3,4-b)pyridine → 4-Piperazin-1-yl-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidine

HRID 1027904Notes

Reaction equation

HRID 1027904 reaction equation
[N:1]1([C:10](OC(C)(C)C)=O)CCCC2[CH2:7][NH:8][CH2:9][CH:2]12.CC1C=CC(S(O[C:28]2[C:29]3[CH2:39][CH2:38][CH2:37][C:36]4[CH:40]=[CH:41][CH:42]=[CH:43][C:35]=4[C:30]=3[N:31]=[C:32](N)[N:33]=2)(=O)=O)=CC=1>>[N:1]1([C:28]2[C:29]3[CH2:39][CH2:38][CH2:37][C:36]4[CH:40]=[CH:41][CH:42]=[CH:43][C:35]=4[C:30]=3[N:31]=[CH:32][N:33]=2)[CH2:2][CH2:9][NH:8][CH2:7][CH2:10]1

Participants

3

Reactant 2

HCID 225622021-Boc-octahydropyrrolo(3,4-b)pyridineHCID 251291732-amino-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-yl 4-methylbenzenesulfonate

Product 1

HCID 250725784-Piperazin-1-yl-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidine

Procedure

The title compound was prepared using the procedure outlined in Example 59D substituting piperazine for t-butyl octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate, and substituting the product from Example 118C for the product from Example 59C. The product was purified by chromatography on silica gel eluting with NH4OH:MeOH:CHCl3 (0.8:8:92) to provide the title compound. 1H NMR (CD3OD) δ 2.32-2.49 (m, 4H), 2.63-2.70 (m, 2H), 2.94-3.01 (m, 4H), 3.47-3.54 (m, 4H), 7.30-7.35 (m, 1H), 7.39-7.44 (m, 2H), 7.65-7.71 (m, 1H), 8.58-8.61 (m, 1H). MS (M+H)+ m/z 281.

Workup

  1. customThe title compound was prepared
  2. customThe product was purified by chromatography on silica gel eluting with NH4OH:MeOH:CHCl3 (0.8:8:92)

Sources & evidence

ORD record
ord-c7fe8d0047264940830042555733f5e4
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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