(1R,4R,7R)-2-azabicyclo[2.2.1]heptan-7-ol → 7-cycloheptyl-2-(5-((1R,4R,7R)-7-hydroxy-2-azabicyclo[2.2.1]heptane-2-carbonyl)pyridin-2-ylamino)-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide

HRID 627337Notes

Reaction equation

HRID 627337 reaction equation
[CH:1]1([N:8]2[C:12]3[N:13]=[C:14]([NH:17][C:18]4[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][N:19]=4)[N:15]=[CH:16][C:11]=3[CH:10]=[C:9]2[C:27](=[O:31])[N:28]([CH3:30])[CH3:29])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C@H:32]12[C@H:38]([OH:39])[C@H:35]([CH2:36][CH2:37]1)[CH2:34][NH:33]2>>[CH:1]1([N:8]2[C:12]3[N:13]=[C:14]([NH:17][C:18]4[CH:26]=[CH:25][C:21]([C:22]([N:33]5[CH2:34][C@@H:35]6[C@@H:38]([OH:39])[C@H:32]5[CH2:37][CH2:36]6)=[O:24])=[CH:20][N:19]=4)[N:15]=[CH:16][C:11]=3[CH:10]=[C:9]2[C:27]([N:28]([CH3:30])[CH3:29])=[O:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 55298875(1R,4R,7R)-2-azabicyclo[2.2.1]heptan-7-olHCID 673554046-(7-Cycloheptyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-nicotinic acid

Product 1

HCID 673554037-cycloheptyl-2-(5-((1R,4R,7R)-7-hydroxy-2-azabicyclo[2.2.1]heptane-2-carbonyl)pyridin-2-ylamino)-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamideYield 77%

Procedure

Following general amide formation method 3, 6-(7-cycloheptyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinic acid was combined with (1R,4R,7R)-2-azabicyclo[2.2.1]heptan-7-ol which gave 7-cycloheptyl-2-(5-((1R,4R,7R)-7-hydroxy-2-azabicyclo[2.2.1]heptane-2-carbonyl)pyridin-2-ylamino)-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (50 mg) in 77% yield.

Sources & evidence

ORD record
ord-93697f96f69f4b35b3d14aa4d815b52c
Source dataset
uspto-grants-2016_04
Patent number
US09309252B2

Reaction notes

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