2-Propanesulfonyl chloride → (R)-4-((R)-1-((3-cyclopropyl-6-(4-(4-(isopropylsulfonyl)piperazin-1-yl)phenyl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one

HRID 2209170Notes

Reaction equation

HRID 2209170 reaction equation
C1(N2C3C(O[C@@H]([C@H]4CNC(=O)C4)C)=NC(C4C=CC(N5CCN(S(C)(=O)=O)CC5)=CC=4)=CC=3N=C2)CC1.[CH:38]1([N:41]2[C:45]3[C:46]([O:62][C@@H:63]([C@H:65]4[CH2:69][NH:68][C:67](=[O:70])[CH2:66]4)[CH3:64])=[N:47][C:48]([C:50]4[CH:55]=[CH:54][C:53]([N:56]5[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]5)=[CH:52][CH:51]=4)=[CH:49][C:44]=3[N:43]=[CH:42]2)[CH2:40][CH2:39]1.[CH3:71][CH:72]([S:74](Cl)(=[O:76])=[O:75])[CH3:73]>>[CH:38]1([N:41]2[C:45]3[C:46]([O:62][C@@H:63]([C@H:65]4[CH2:69][NH:68][C:67](=[O:70])[CH2:66]4)[CH3:64])=[N:47][C:48]([C:50]4[CH:55]=[CH:54][C:53]([N:56]5[CH2:61][CH2:60][N:59]([S:74]([CH:72]([CH3:73])[CH3:71])(=[O:76])=[O:75])[CH2:58][CH2:57]5)=[CH:52][CH:51]=4)=[CH:49][C:44]=3[N:43]=[CH:42]2)[CH2:39][CH2:40]1

Participants

4

Reactant 3

HCID 824082-Propanesulfonyl chlorideHCID 117843096HCID 117843096, compoundHCID 117844129HCID 117844129, compound

Product 1

HCID 117844030(R)-4-((R)-1-((3-cyclopropyl-6-(4-(4-(isopropylsulfonyl)piperazin-1-yl)phenyl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-oneYield 15%

Procedure

Following the procedure described for intermediate 3.45, starting from (R)-4-((R)-1-((3-cyclopropyl-6-(4-(piperazin-1-yl)phenyl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one (90 mg, 0.2 mmol) and propane-2-sulfonyl chloride (0.02 ml, 0.22 mmol) to provide 16.6 mg of (R)-4-((R)-1-((3-cyclopropyl-6-(4-(4-(isopropylsulfonyl)piperazin-1-yl)phenyl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one.

Sources & evidence

ORD record
ord-b3eee475ca4a45ba9480573c6f8508b4
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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