Cyanogen Bromide → HCID 118599062, compound

HRID 1050354Notes

Reaction equation

HRID 1050354 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[C:14](=[O:15])[N:13]3[C:16]([CH:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)([CH3:20])[NH:17][C:18](=[O:19])[C:12]3=[CH:11][CH:10]=2)[CH:3]=1.[H-].[Na+].[N:28]#[C:29]Br>O1CCCC1>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[C:14](=[O:15])[N:13]3[C:16]([CH:21]4[CH2:22][CH2:23][CH2:24][CH2:25]4)([CH3:20])[N:17]([C:29]#[N:28])[C:18](=[O:19])[C:12]3=[CH:11][CH:10]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 24758Sodium hydrideHCID 118598567HCID 118598567, compound

Product 1

HCID 118599062HCID 118599062, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a 2-neck round bottom flask 6-[(6-aminopyrimidin-4-yl)amino]-3-cyclopentyl-3-methyl-2H-imidazo[1,5-a]pyridine-1,5-dione (2, 0.28 g, 0.82 mmol) was taken in dry tetrahydrofuran (15 mL). The reaction mixture was cooled to 0° C. and sodium hydride (164 mg, 4.11 mmol) was added in portions. After stirring for 10 min at room temperature, cyanogen bromide (436 mg, 4.11 mmol) was added and the resulting reaction mixture was stirred at room temperature for 20 h. The reaction mixture was quenched with aqueous ammonium chloride solution and then concentrated to get the crude mass. This crude was purified by flash chromatography eluting with 2% methanol in dichloromethane. The compound was washed with pentane and dried under vacuum to afford 6-[(6-aminopyrimidin-4-yl)amino]-3-cyclopentyl-3-methyl-1,5-dioxo-imidazo[1,5-a]pyridine-2-carbonitrile (Cpd. No. 118) as yellow solid. Yield: 0.018 g, 6%; MS (ESI) m/z 366.16 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 9.08 (s, 1H), 8.71 (d, J=7.84, 1H), 8.19 (s, 1H), 7.28 (d, J=7.96, 1H), 6.65 (s, 2H), 6.29 (s, 1H), 3.49-3.43 (m, 1H), 2.21 (s, 3H), 1.94 (m, 1H), 1.7-1.58 (m, 4H), 1.48 (m, 1H), 1.23 (m, 1H), 1.06-1.02 (m, 1H).

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred at room temperature for 20 h
  3. customThe reaction mixture was quenched with aqueous ammonium chloride solution
  4. concentrationconcentrated
  5. customto get the crude mass
  6. customThis crude was purified by flash chromatography
  7. washeluting with 2% methanol in dichloromethane
  8. washThe compound was washed with pentane
  9. customdried under vacuum

Sources & evidence

ORD record
ord-9f3d27e57d614a2fb23561476dd4f4a4
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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