Lithium Chloride → HCID 53378789, compound

HRID 1850569Notes

Reaction equation

HRID 1850569 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]([OH:22])=O)=[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.[Li+].[Cl-].[CH3:32][C:33]12[CH:41]([OH:42])[C:37]([CH3:43])([CH2:38][NH:39][CH2:40]1)[CH2:36][N:35]([CH3:44])[CH2:34]2>>[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]([N:39]5[CH2:40][C:33]6([CH3:32])[CH:41]([OH:42])[C:37]([CH3:43])([CH2:36][N:35]([CH3:44])[CH2:34]6)[CH2:38]5)=[O:22])=[CH:18][N:17]=4)[N:13]=[CH:14][C:9]=3[CH:8]=[C:7]2[C:25]([N:26]([CH3:28])[CH3:27])=[O:29])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 433294Lithium ChlorideHCID 5415011,3,5-Trimethyl-3,7-diazabicyclo[3.3.1]nonan-9-olHCID 583154726-(7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinic acid

Product 1

HCID 53378789HCID 53378789, compoundYield 68%

Procedure

Following amide formation method 1, 6-(7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinic acid with 5 equiv LiCl and 1,3,5-trimethyl-3,7-diazabicyclo[3.3.1]nonan-9-ol were combined and gave 7-cyclopentyl-2-(5-(9-hydroxy-1,5,7-trimethyl-3,7-diazabicyclo[3.3.1]nonane-3-carbonyl)pyridin-2-ylamino)-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (266 mg) in 68% yield. 1H NMR (400 MHz, CDCl3) δ ppm 8.77 (s, 1H), 8.56 (d, J=8.6 Hz, 1H), 8.33 (s, 1H), 8.17 (br s, 1H), 7.72 (d, J=8.6 Hz, 1H), 6.49 (s, 1H), 4.81 (m, 2H), 3.74 (br m, 1H), 3.26 (s, 1H), 3.18 (s, 6H), 3.07 (br m, 1H), 2.70-2.56 (m, 4H), 2.29 (br m, 3H), 2.19 (s, 3H), 2.15-2.03 (m, 4H), 1.89 (m, 1H), 1.75 (m, 2H), 1.00 (br s, 3H), 0.83 (br s 3H)

Sources & evidence

ORD record
ord-7d56085f24464fb18a3d3f21ac175dc6
Source dataset
uspto-grants-2015_02
Patent number
US08957074B2

Reaction notes

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