8-Boc-3,8-diaza-bicyclo(3.2.1)octane → HCID 67239739, compound

HRID 1853183Notes

Reaction equation

HRID 1853183 reaction equation
[CH3:1][N:2]([CH3:28])[C:3]([C:5]1[N:22]([CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[C:8]2[N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([CH:20]=O)=[CH:16][N:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].[C:29]([O:33][C:34]([N:36]1[CH:41]2[CH2:42][CH2:43][CH:37]1[CH2:38][NH:39][CH2:40]2)=[O:35])([CH3:32])([CH3:31])[CH3:30]>>[C:29]([O:33][C:34]([N:36]1[CH:37]2[CH2:43][CH2:42][CH:41]1[CH2:40][N:39]([CH2:20][C:17]1[CH:16]=[N:15][C:14]([NH:13][C:10]3[N:11]=[CH:12][C:7]4[CH:6]=[C:5]([C:3](=[O:4])[N:2]([CH3:28])[CH3:1])[N:22]([CH:23]5[CH2:24][CH2:25][CH2:26][CH2:27]5)[C:8]=4[N:9]=3)=[CH:19][CH:18]=1)[CH2:38]2)=[O:35])([CH3:32])([CH3:30])[CH3:31]

Participants

3

Reactant 2

HCID 157409088-Boc-3,8-diaza-bicyclo(3.2.1)octaneHCID 583154407-cyclopentyl-2-(5-formyl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide

Product 1

HCID 67239739HCID 67239739, compound

Procedure

Following General Procedure B, 7-cyclopentyl-2-(5-formyl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (0.153 g, 0.405 mmol) and 3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (95 mg, 0.445 mmol) gave 3-[6-(7-cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridin-3-ylmethyl]-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester as an off white solid (0.186 g, 80%) [following purification by SiO2 chromatography, eluting with 0-5% MeOH/EtOAc]. MS (ESI) m/z 575.3 (M+H)+

Sources & evidence

ORD record
ord-8f5716578dd349549e9a5a37d83919f0
Source dataset
uspto-grants-2015_02
Patent number
US08962630B2

Reaction notes

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