Picolinic acid → 4-(4,7-Diaza-spiro[2.5]oct-7-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 527888Notes

Reaction equation

HRID 527888 reaction equation
CC(C)(C(=O)[N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[CH2:8][N:9]([C:14]1[C:15]3[CH:22]=[CH:21][NH:20][C:16]=3[N:17]=[CH:18][N:19]=1)[CH2:10]2)C#N.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1C=CC=CC=1C(O)=O>CN(C=O)C>[CH2:12]1[C:11]2([CH2:10][N:9]([C:14]3[C:15]4[CH:22]=[CH:21][NH:20][C:16]=4[N:17]=[CH:18][N:19]=3)[CH2:8][CH2:7][NH:6]2)[CH2:13]1

Participants

6

Reactant 4

HCID 1018Picolinic acidHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 668883222,2-Dimethyl-3-oxo-3-[3-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diaza-bicyclo[3.2.1]oct-8-yl]-propionitrile

Product 1

HCID 668882444-(4,7-Diaza-spiro[2.5]oct-7-yl)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(intermediate 2) (0.05 mmol) was dissolved in dry DMF (0.3 mL). Triethylamine (0.18 mmol) and HATU (0.09 mmol) was added followed by 2-pyridincarboxylic acid (0.07 mmol). The reaction mixture was left at rt for 16 hours. The pure compounds were obtained by standard preparative HPLC purification of the reaction mixture.

Workup

  1. customThe pure compounds were obtained by standard preparative HPLC purification of the reaction mixture

Sources & evidence

ORD record
ord-61b67ac6a7ac4792b5748afe4127d130
Source dataset
uspto-grants-2016_05
Patent number
US09346809B2

Reaction notes

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