Trifluoroacetic acid → 7-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonic acid bis-(3-cyano-propyl)-amide

HRID 589973Notes

Reaction equation

HRID 589973 reaction equation
C(OC([N:8]1[C:12]2[N:13]=[CH:14][N:15]=[C:16]([N:17]3[CH2:24][C:21]4([CH2:23][CH2:22]4)[N:20]([S:25](=[O:38])(=[O:37])[N:26]([CH2:32][CH2:33][CH2:34][C:35]#[N:36])[CH2:27][CH2:28][CH2:29][C:30]#[N:31])[CH2:19][CH2:18]3)[C:11]=2[CH:10]=[CH:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C1COCC1>[C:30]([CH2:29][CH2:28][CH2:27][N:26]([CH2:32][CH2:33][CH2:34][C:35]#[N:36])[S:25]([N:20]1[CH2:19][CH2:18][N:17]([C:16]2[C:11]3[CH:10]=[CH:9][NH:8][C:12]=3[N:13]=[CH:14][N:15]=2)[CH2:24][C:21]21[CH2:23][CH2:22]2)(=[O:38])=[O:37])#[N:31]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 682960054-{4-[Bis-(3-cyano-propyl)-sulfamoyl]-4,7-diaza-spiro[2.5]oct-7-yl}-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester2×

Product 1

HCID 574106987-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonic acid bis-(3-cyano-propyl)-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-{4-[Bis-(3-cyano-propyl)-sulfamoyl]-4,7-diaza-spiro[2.5]oct-7-yl}-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester (intermediate 19) was dissolved in THF (1 mL), added TFA (0.5 mL) and then stirred at rt for 2 h. The crude reaction mixture was concentrated in vacuo and redissolved in MeOH (0.5 mL). The pure compound was obtained by standard preparative HPLC purification of the reaction mixture.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated in vacuo
  3. dissolutionredissolved in MeOH (0.5 mL)
  4. customThe pure compound was obtained by standard preparative HPLC purification of the reaction mixture

Sources & evidence

ORD record
ord-4037e1dfea054296a53ef464999180dc
Source dataset
uspto-grants-2016_01
Patent number
US09233964B2

Reaction notes

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