Piperidine → HCID 131736565, compound

HRID 1479109Notes

Reaction equation

HRID 1479109 reaction equation
N1CCCCC1.C1C2C(COC([N:24]3[CH:29]4[CH2:30][N:31]([CH2:33][C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=5[C:40]([N:42]5[CH2:56][C:45]6=[C:46]7[N:51]([N:52]=[C:44]6[CH2:43]5)[C:50]([CH3:53])=[C:49]([Cl:54])[C:48]([CH3:55])=[N:47]7)=[O:41])[CH2:32][CH:25]3[CH2:26][O:27][CH2:28]4)=O)C3C(=CC=CC=3)C=2C=CC=1>CN(C=O)C.O>[ClH:54].[ClH:54].[Cl:54][C:49]1[C:48]([CH3:55])=[N:47][C:46]2[N:51]([N:52]=[C:44]3[CH2:43][N:42]([C:40]([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=4[CH2:33][N:31]4[CH2:32][CH:25]5[NH:24][CH:29]([CH2:28][O:27][CH2:26]5)[CH2:30]4)=[O:41])[CH2:56][C:45]3=2)[C:50]=1[CH3:53]

Participants

5

Reactant 2

HCID 8082PiperidineHCID 131736566HCID 131736566, compound

Product 1

HCID 131736565HCID 131736565, compoundYield 214.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Piperidine (0.4 mL) was added to a solution of 7-[2-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-benzyl]-3-oxa-7,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid 9H-fluoren-9-ylmethyl ester (354 mg, 0.44 mmol) in DMF (4 mL). The resulting mixture was stirred at RT for 30 min, then diluted with water (20 mL). The precipitate was filtered off and washed with water (2×). After purification by flash chromatography (silica, DCM/EtOH/28% aqueous ammonia), the parent compound was dissolved in water (8 ml) and the solution was lyophilized to give the title compound as a yellow solid (170 mg, 72%). 1H NMR (300 MHz, DMSO-d6) δ 10.92 (br s, 2H), 10.01 (br s, 1H), 7.95-7.78 (m, 2H), 7.72-7.60 (m, 2H), 5.01 (s, 1H), 4.99 (s, 1H), 4.85 (s, 1H), 4.80 (s, 1H), 4.46 (s, 2H), 4.19-4.04 (m, 4H), 3.97-3.70 (m, 6H), 2.86 (s, 1.5H), 2.82 (s, 1.5H), 2.63 (s, 1.5H), 2.57 (s, 1.5H). HPLC (max plot) 100%, Rt 2.26 min. UPLC/MS: (MS+) 467.3 ([M+H]+), (MS−) 465.4 ([M−H]−).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water (2×)
  3. customAfter purification by flash chromatography (silica, DCM/EtOH/28% aqueous ammonia)
  4. dissolutionthe parent compound was dissolved in water (8 ml)

Sources & evidence

ORD record
ord-2d2e57676e634bccb0c9043524e143a6
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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