Methyl triflate → 4-[4-(Piperidine-1-sulfonyl)-4,7-diaza-spiro[2.5]oct-7-yl]-7H-pyrrolo[2,3-d]pyrimidine

HRID 589968Notes

Reaction equation

HRID 589968 reaction equation
N1([S:6]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)(=[O:8])=[O:7])C=CN=C1.COS(C(F)(F)F)(=O)=O.[CH2:24]1[C:26]2([CH2:31][N:30]([C:32]3[C:33]4[CH:40]=[CH:39][NH:38][C:34]=4[N:35]=[CH:36][N:37]=3)[CH2:29][CH2:28][NH:27]2)[CH2:25]1>C(Cl)Cl.CS(C)=O>[N:9]1([S:6]([N:27]2[CH2:28][CH2:29][N:30]([C:32]3[C:33]4[CH:40]=[CH:39][NH:38][C:34]=4[N:35]=[CH:36][N:37]=3)[CH2:31][C:26]32[CH2:24][CH2:25]3)(=[O:8])=[O:7])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 3

HCID 9526Methyl triflateHCID 29901621-(Imidazole-1-sulfonyl)-piperidine2×HCID 668882444-(4,7-Diaza-spiro[2.5]oct-7-yl)-7H-pyrrolo[2,3-d]pyrimidine2×

Product 1

HCID 574105714-[4-(Piperidine-1-sulfonyl)-4,7-diaza-spiro[2.5]oct-7-yl]-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(imidazole-1-sulfonyl)-piperidine (intermediate 13) (0.047 mmol) in dry CH2Cl2 (1 mL) was cooled to 0° C. and added trifluoro-methanesulfonic acid methyl ester (0.047 mmol). The reaction mixture was allowed to warm up freely to rt over a period of 4 h and then concentrated in vacuo. The residual oil was redissolved in dry CH3CN (1.5 mL), added a solution of 4-(4,7-diaza-spiro[2.5]oct-7-yl)-7H-pyrrolo[2,3-d]pyrimidine (intermediate 21) (0.047 mmol) in DMSO (1 mL) and then stirred at 50° C. for 3 h. The pure compound was obtained by standard preparative HPLC purification of the reaction mixture.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residual oil was redissolved in dry CH3CN (1.5 mL)
  3. customThe pure compound was obtained by standard preparative HPLC purification of the reaction mixture

Sources & evidence

ORD record
ord-4b3909a539534107bae9adc235d5aba5
Source dataset
uspto-grants-2016_01
Patent number
US09233964B2

Reaction notes

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