(4,4-Difluoropiperidin-1-yl)[5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]methanone → [6-chloro-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanone

HRID 19882Notes

Reaction equation

HRID 19882 reaction equation
FC1(F)CCN(C(C2NC3C(C=2)=CC(OC2CCN(C(C)C)CC2)=CC=3)=O)CC1.Cl.ClC1C=C2C(C=C(C(O)=O)N2)=CC=1OC1CCN(C(C)C)CC1.[Cl:54][C:55]1[CH:63]=[C:62]2[C:58]([CH:59]=[C:60]([C:70]([N:72]3[CH2:77][CH2:76][C:75]([F:79])([F:78])[CH2:74][CH2:73]3)=[O:71])[N:61]2C2C=NC=NC=2)=[CH:57][C:56]=1[O:80][CH:81]1[CH2:86][CH2:85][N:84]([CH:87]([CH3:89])[CH3:88])[CH2:83][CH2:82]1>>[Cl:54][C:55]1[CH:63]=[C:62]2[C:58]([CH:59]=[C:60]([C:70]([N:72]3[CH2:77][CH2:76][C:75]([F:78])([F:79])[CH2:74][CH2:73]3)=[O:71])[NH:61]2)=[CH:57][C:56]=1[O:80][CH:81]1[CH2:82][CH2:83][N:84]([CH:87]([CH3:89])[CH3:88])[CH2:85][CH2:86]1

Participants

4

Reactant 3

HCID 11603838(4,4-Difluoropiperidin-1-yl)[5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]methanoneHCID 16739632[6-Chloro-5-(1-isopropyl-piperidin-4-yloxy)-1-pyrimidin-5-yl-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanoneHCID 670179056-Chloro-5-(1-isopropyl-piperidin-4-yloxy)-1h-indole-2-carboxylic acid hydrochloride salt

Product 1

HCID 67017927[6-chloro-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanone

Procedure

In analogy to the procedure described for the synthesis of intermediate 1, step 4, the title compound was synthesized from 6-chloro-5-(1-isopropyl-piperidin-4-yloxy)-1H-indole-2-carboxylic acid hydrochloride salt with 1 eq. lithium chloride (example 39, step 4). The title compound was obtained in 70% yield as light yellow solid. MS (m/e): 440.3 (MH+, 100%).

Sources & evidence

ORD record
ord-92ca1d9978b9428d827f457da017c8d0
Source dataset
uspto-grants-2010_06
Patent number
US07745479B2

Reaction notes

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