HCID 118598573, compound → HCID 118598572, compound

HRID 1050357Notes

Reaction equation

HRID 1050357 reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([NH:10][C:11]2[C:16](=[O:17])[N:15]3[C:18]4([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)[NH:19][C:20](=[O:21])[C:14]3=[C:13]([Cl:27])[CH:12]=2)=[N:3][CH:2]=1>CO.O1CCOCC1>[ClH:27].[Cl:27][C:13]1[CH:12]=[C:11]([NH:10][C:4]2[C:5]3[CH:9]=[CH:8][NH:7][C:6]=3[N:1]=[CH:2][N:3]=2)[C:16](=[O:17])[N:15]2[C:18]3([NH:19][C:20](=[O:21])[C:14]=12)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3

Participants

4

Reactant 1

HCID 118598573HCID 118598573, compound

Product 1

HCID 118598572HCID 118598572, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 8-chloro-6-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)spiro[2H-imidazo[1,5-a]pyridine-3,1′-cyclohexane]-1,5-dione (3, 0.6 g, 1.56 mmol) in methanol (6 mL) 4 M hydrogenchloride in dioxane (4 mL) was added under cooling and stirred the reaction mixture at room temperature for overnight. After completion filtered the reaction mass using sintered funnel and washed with ethanol (10 mL). The solid obtained was dried under high vacuum to afford 8-chloro-6-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)spiro[2H-imidazo[1,5-a]pyridine-3,1′-cyclohexane]-1,5-dione hydrochloride (Cpd. No. 123) as light yellow solid; Yield: 0.21 g, 32%; MS (ESI) m/z 385.31 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 12.24 (s, 1H), 10.39 (s, 1H), 9.12 (s, 1H), 8.75 (s, 1H), 8.50 (s, 1H), 7.43 (s, 1H), 6.88 (s, 1H), 2.95 (t, J=11.14 Hz, 2H), 1.76 (m, 2H), 1.62 (m, 5H), 1.22 (m, 1H).

Workup

  1. temperatureunder cooling
  2. filtrationAfter completion filtered the reaction mass
  3. washwashed with ethanol (10 mL)
  4. customThe solid obtained
  5. customwas dried under high vacuum

Sources & evidence

ORD record
ord-5a69ddbd2d7f4bb39eb8438a08c13716
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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