(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-hydroxy-4-methyl-piperidin-1-yl)-methanone

HRID 19883Notes

Reaction equation

HRID 19883 reaction equation
FC1(F)CCN(C(C2NC3C(C=2)=CC(OC2CCN(C(C)C)CC2)=CC=3)=O)CC1.Cl.[Cl:31][C:32]1[CH:40]=[C:39]2[C:35]([CH:36]=[C:37]([C:41](O)=[O:42])[NH:38]2)=[CH:34][C:33]=1[O:44][CH:45]1[CH2:50][CH2:49][N:48]([CH:51]([CH3:53])[CH3:52])[CH2:47][CH2:46]1.ClC1C=C2C(C=C(C(N3CCC(F)(F)CC3)=O)N2C2C=NC=NC=2)=CC=1OC1CCN(C(C)C)CC1.[CH3:90][C:91]1([OH:97])[CH2:96][CH2:95][NH:94][CH2:93][CH2:92]1>>[Cl:31][C:32]1[CH:40]=[C:39]2[C:35]([CH:36]=[C:37]([C:41]([N:94]3[CH2:95][CH2:96][C:91]([OH:97])([CH3:90])[CH2:92][CH2:93]3)=[O:42])[NH:38]2)=[CH:34][C:33]=1[O:44][CH:45]1[CH2:46][CH2:47][N:48]([CH:51]([CH3:52])[CH3:53])[CH2:49][CH2:50]1

Participants

5

Reactant 4

HCID 11603838(4,4-Difluoropiperidin-1-yl)[5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]methanoneHCID 156491744-Methylpiperidin-4-olHCID 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 67017915[6-Chloro-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4-hydroxy-4-methyl-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) and 4-methyl-piperidin-4-ol (CAS Nr. 3970-68-1). The title compound was obtained in 72% yield as yellow foam. MS (m/e): 434.3 (MH+, 100%).

Sources & evidence

ORD record
ord-e6aa30bdc4aa4e45ad69f4f9500de45f
Source dataset
uspto-grants-2010_06
Patent number
US07745479B2

Reaction notes

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