1,4-Diazabicyclo(3.2.2)nonane → HCID 67354865, compound

HRID 1850575Notes

Reaction equation

HRID 1850575 reaction equation
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][N:17]=4)[N:13]=[CH:14][C:9]=3[CH:8]=[C:7]2[C:25](=[O:29])[N:26]([CH3:28])[CH3:27])[CH2:5][CH2:4][CH2:3][CH2:2]1.[N:30]12[CH2:38][CH2:37][CH:34]([CH2:35][CH2:36]1)[NH:33][CH2:32][CH2:31]2>>[CH3:28][N:26]([CH3:27])[C:25]([C:7]1[N:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:10]2[N:11]=[C:12]([NH:15][C:16]3[CH:24]=[CH:23][C:19]([C:20]([N:33]4[CH:34]5[CH2:37][CH2:38][N:30]([CH2:36][CH2:35]5)[CH2:31][CH2:32]4)=[O:21])=[CH:18][N:17]=3)[N:13]=[CH:14][C:9]=2[CH:8]=1)=[O:29]

Participants

3

Reactant 2

HCID 3984071,4-Diazabicyclo(3.2.2)nonaneHCID 583154726-(7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinic acid

Product 1

HCID 67354865HCID 67354865, compoundYield 25.1%

Procedure

Following general amide formation method 1, 6-(7-Cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-nicotinic acid (120 mg, 0.198 mmol, 1.0 eq) was combined with 1,4-Diaza-bicyclo[3.2.2]nonane (43.3 mg, 0.218 mmol, 1.1 eq) which gave 7-cyclopentyl-2-[5-(1,4-diaza-bicyclo[3.2.2]nonane-4-carbonyl)-pyridin-2-ylamino]-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (25 mg) in 23% yield. 1H NMR (400 MHz, CDCl3-d) δ ppm 1.64-1.81 (m, 2H) 1.86 (br. s., 2H) 2.00-2.22 (m, 6H) 2.51-2.70 (m, 2H) 3.03-3.16 (m, 5H) 3.18 (s, 7H) 3.79 (br. s., 2H) 4.83 (quin, J=8.84 Hz, 1H) 6.50 (s, 1H) 7.81 (dd, J=8.84, 2.27 Hz, 1H) 8.35-8.44 (m, 2H) 8.58 (d, J=8.59 Hz, 1H) 8.79 (s, 1H). HRMS m/z, (M+H)+: 503.2891

Sources & evidence

ORD record
ord-d907075b0a0b4e3599b627ca60f4c62f
Source dataset
uspto-grants-2015_02
Patent number
US08957074B2

Reaction notes

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