Lithium Chloride → HCID 67379584, compound

HRID 627366Notes

Reaction equation

HRID 627366 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.[Li+].[Cl-].[C@@H:32]12[NH:47][C@@H:36]([CH2:37][N:38]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:39]1)[CH2:35][O:34][CH2:33]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:47]5[C@H:32]6[CH2:39][N:38]([C:40]([O:42][C:43]([CH3:44])([CH3:46])[CH3:45])=[O:41])[CH2:37][C@@H:36]5[CH2:35][O:34][CH2:33]6)=[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]([CH3:27])[CH3:28])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 3

HCID 433294Lithium ChlorideHCID 583154726-(7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinic acidHCID 86686636HCID 86686636, compound

Product 1

HCID 67379584HCID 67379584, compoundYield 85%

Procedure

Following general amide formation method 2, 6-(7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinic acid with 5 equiv LiCl and (1R,5S)-tert-butyl 3-oxa-7,9-diazabicyclo[3.3.1]nonane-7-carboxylate were combined and gave (1R,5S)-tert-butyl 9-(6-(7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinoyl)-3-oxa-7,9-diazabicyclo[3.3.1]nonane-7-carboxylate (115 mg) in 85% yield. 1H NMR (400 MHz, CDCl3) δ ppm 8.78 (s, 1H), 8.60 (d, J=9.09 Hz, 1H), 8.44 (d, J=2.02 Hz, 2H), 7.85 (dd, J1=8.59 Hz, J2=2.02 Hz, 1H), 6.49 (s, 1H), 4.82 (m, 1H), 4.59-3.75 (m, 6H), 3.17 (s, 4H), 3.02 (s, 2H), 2.95 (s, 2H), 2.81 (m, 4H), 2.57 (m, 1H), 2.09 (m, 4H), 1.75 (m, 1H), 1.49 (m, 9H) LCMS m/z 604.9 (M+H)+.

Sources & evidence

ORD record
ord-e9f5674ed339471cbef7ea9436c49fe4
Source dataset
uspto-grants-2016_04
Patent number
US09309252B2

Reaction notes

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