Pyridine → HCID 178441564, compound

HRID 746528Notes

Reaction equation

HRID 746528 reaction equation
O[N:2]1[C:24](=O)[NH:23][C@H:22]2[C@@H:3]1[CH2:4][S:5][C@H:6]2[CH2:7][CH2:8][CH2:9][C:10](=NN1C(=O)CCC1=O)[C:11](=[O:13])O.[NH2:26][CH2:27][CH2:28][N:29]1[C:41]2[C:40]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[N:34]=[C:33]([NH2:42])[C:32]=2[N:31]=[C:30]1[CH2:43][CH2:44][CH2:45][CH3:46].[N:47]1C=CC=CC=1>>[NH2:42][C:33]1[C:32]2[N:31]=[C:30]([CH2:43][CH2:44][CH2:45][CH3:46])[N:29]([CH2:28][CH2:27][NH:26][C:11](=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]3[CH:22]4[CH:3]([NH:2][C:24](=[NH:47])[NH:23]4)[CH2:4][S:5]3)[C:41]=2[C:40]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[N:34]=1

Participants

4

Reactant 3

HCID 1049Pyridine2×HCID 22180889HCID 22180889, compoundHCID 131723488HCID 131723488, compound

Product 1

HCID 178441564HCID 178441564, compound

Procedure

A solution of N-hydroxysuccinimidoiminobiotin (0.74 g, 1.76 mmol) in pyridine (10 mL) was slowly added to a solution of 1-(2-aminoethyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine (0.50 g, 1.76 mmol) in pyridine (30 mL). The reaction was maintained at ambient temperature overnight and then concentrated to dryness. The residue was partitioned between dichloromethane and aqueous saturated potassium carbonate. The organic layer was dried over magnesium sulfate and then concentrated to dryness. The residue was recrystallized from ethanol to provide 0.5 g of N1-[2-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-5-(2-iminoperhydrothieno[3,4-d]imidazol-4-yl)pentanamide as a solid, m.p. 95-96° C. High resolution mass spec: Theoretical mass=508.2733, Measured mass=508.2723.

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was partitioned between dichloromethane and aqueous saturated potassium carbonate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated to dryness
  5. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-49cdd4b021ab4dd09c218d3612e11316
Source dataset
uspto-grants-2008_07
Patent number
US07393859B2

Reaction notes

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