HCID 67354835, compound → HCID 67355417, compound

HRID 1850654Notes

Reaction equation

HRID 1850654 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[C:15](=[O:16])[CH2:14][CH:13]3[N:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:10]([CH2:11][CH2:12]3)[CH2:9]2)=[CH:4][CH:3]=1.Cl[C:26]1[N:27]=[CH:28][C:29]2[CH:34]=[C:33]([C:35]([N:37]([CH3:39])[CH3:38])=[O:36])[N:32]([CH:40]3[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]3)[C:30]=2[N:31]=1>>[CH:40]1([N:32]2[C:30]3[N:31]=[C:26]([NH:1][C:2]4[N:7]=[CH:6][C:5]([N:8]5[C:15](=[O:16])[CH2:14][CH:13]6[N:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:10]([CH2:11][CH2:12]6)[CH2:9]5)=[CH:4][CH:3]=4)[N:27]=[CH:28][C:29]=3[CH:34]=[C:33]2[C:35](=[O:36])[N:37]([CH3:38])[CH3:39])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]1

Participants

3

Reactant 2

HCID 67354835HCID 67354835, compoundHCID 86686647HCID 86686647, compound

Product 1

HCID 67355417HCID 67355417, compoundYield 55.2%

Procedure

Following general N—C coupling procedure 1, tert-butyl 3-(6-aminopyridin-3-yl)-4-oxo-3,9-diazabicyclo[4.2.1]nonane-9-carboxylate (120 mg, 0.361 mmol) was combined with 2-chloro-7-cyclohexyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (111 mg, 0.361 mmol) which gave tert-butyl 3-(6-(7-cyclohexyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)pyridin-3-yl)-4-oxo-3,9-diazabicyclo[4.2.1]nonane-9-carboxylate (120 mg) in 55.1% yield. MS m/z 603.6 (M+H)+.

Sources & evidence

ORD record
ord-03a46cc9d58549fc9113567e460a32df
Source dataset
uspto-grants-2015_02
Patent number
US08957074B2

Reaction notes

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