2-Pyrrolidone → (4R)-4-((1R)-1-((3-cyclopropyl-6-(4-(6-(oxetan-3-yl)-3,6-diazabicyclo[3.1.1]heptan-3-yl)phenyl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one

HRID 2209108Notes

Reaction equation

HRID 2209108 reaction equation
N1C[CH2:4][CH2:3][C:2]1=[O:6].BrC1C=CC(C2CCN(C3COC3)CC2)=CC=1.[CH:24]12[CH2:30][CH:28]([NH:29]1)[CH2:27][N:26]([C:31]1[CH:36]=[CH:35][C:34]([C:37]3[N:42]=[C:41]([O:43][C@@H:44]([C@H:46]4[CH2:50][NH:49][C:48](=[O:51])[CH2:47]4)[CH3:45])[C:40]4[N:52]([CH:55]5[CH2:57][CH2:56]5)[CH:53]=[N:54][C:39]=4[CH:38]=3)=[CH:33][CH:32]=1)[CH2:25]2>>[CH:55]1([N:52]2[C:40]3[C:41]([O:43][C@@H:44]([C@H:46]4[CH2:50][NH:49][C:48](=[O:51])[CH2:47]4)[CH3:45])=[N:42][C:37]([C:34]4[CH:33]=[CH:32][C:31]([N:26]5[CH2:25][CH:24]6[CH2:30][CH:28]([N:29]6[CH:3]6[CH2:4][O:6][CH2:2]6)[CH2:27]5)=[CH:36][CH:35]=4)=[CH:38][C:39]=3[N:54]=[CH:53]2)[CH2:57][CH2:56]1

Participants

4

Reactant 3

HCID 120252-PyrrolidoneHCID 117843098(4R)-4-((1R)-1-((6-(4-(3,6-diazabicyclo[3.1.1]heptan-3-yl)phenyl)-3-cyclopropyl-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-oneHCID 1178437314-(4-Bromophenyl)-1-(oxetan-3-yl)piperidine

Product 1

HCID 117844064(4R)-4-((1R)-1-((3-cyclopropyl-6-(4-(6-(oxetan-3-yl)-3,6-diazabicyclo[3.1.1]heptan-3-yl)phenyl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-oneYield 11%

Procedure

Preparation of (4R)-4-0R)-1-((3-cyclopropyl-6-(4-(6-(oxetan-3-yl)-3,6-diazabicyclo[3.1.1]heptan-3-yl)phenyl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one: Prepared by the procedure, previously described for the synthesis of 4-(4-bromophenyl)-1-(oxetan-3-yl)piperidine, using instead (4R)-4-((1R)-1-((6-(4-(3,6-diazabicyclo[3.1.1]heptan-3-yl)phenyl)- 3-cyclopropyl-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one: as a starting material to afford 10.1 mg (11%) of (4R)-4-((1R)-1-((3-cyclopropyl-6-(4-(6-(oxetan-3-yl)-3,6-diazabicyclo[3.1.1]heptan-3-yl)phenyl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one:. 1H NMR (300 MHz, d6-DMSO) δ 8.22 (s, 1H), 7.98 (d, J=8.8 Hz, 2H), 7.61 (s, 1H), 7.57 (s, 1H), 6.78 (d, J=8.8 Hz, 2H), 5.57 (m, 1H), 4.57 (m, 2H), 4.27 (m, 2H), 3.78 (m, 4H), 3.42 (m, 1H), 3.22 (m, 2H), 2.84 (m, 1H), 2.34 (m, 3H), 1.53 (m, 1H), 1.41 (d, J=6.3 Hz, 3H), 1.18 (m, 7H). MS (ESI+) m/z 515.1 (M+H).

Workup

  1. customPrepared by the procedure

Sources & evidence

ORD record
ord-ac5573abba1c4d9f8fdbd970d2b08650
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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