HCID 67354835, compound → HCID 67379605, compound

HRID 1850652Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH:14]2[CH2:15][CH2:16][CH:9]1[CH2:10][N:11]([C:18]1[CH:19]=[N:20][C:21]([NH2:24])=[CH:22][CH:23]=1)[C:12](=[O:17])[CH2:13]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:25][N:26]([CH3:50])[C:27]([C:29]1[N:38]([C:39]2[CH:44]=[CH:43][C:42]([C:45]([C:48]#[N:49])([CH3:47])[CH3:46])=[CH:41][CH:40]=2)[C:32]2[N:33]=[C:34](Cl)[N:35]=[CH:36][C:31]=2[CH:30]=1)=[O:28]>>[C:48]([C:45]([C:42]1[CH:41]=[CH:40][C:39]([N:38]2[C:32]3[N:33]=[C:34]([NH:24][C:21]4[N:20]=[CH:19][C:18]([N:11]5[C:12](=[O:17])[CH2:13][CH:14]6[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH:9]([CH2:16][CH2:15]6)[CH2:10]5)=[CH:23][CH:22]=4)[N:35]=[CH:36][C:31]=3[CH:30]=[C:29]2[C:27](=[O:28])[N:26]([CH3:25])[CH3:50])=[CH:44][CH:43]=1)([CH3:47])[CH3:46])#[N:49]

Participants

Reactant 2

HCID 67354835HCID 67354835, compound

HCID 86686630HCID 86686630, compound

Product 1

HCID 67379605HCID 67379605, compoundYield 89%

Procedure

Following general N—C coupling procedure 1, 3-(6-Amino-pyridin-3-yl)-4-oxo-3,9-diaza-bicyclo[4.2.1]nonane-9-carboxylic acid tert-butyl ester was combined with 2-Chloro-7-[4-(cyano-dimethyl-methyl)-phenyl]-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide which gave tert-butyl 3-(6-(7-(4-(2-cyanopropan-2-yl)phenyl)-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino) pyridin-3-yl)-4-oxo-3,9-diazabicyclo[4.2.1]nonane-9-carboxylate (160 mg) in 89% yield. MS m/z 664.7

Sources & evidence

ORD record: ord-67024caefee144b292a13e40b8d09bc1
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957074B2

Reaction notes

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