HCID 67279564, compound → HCID 59603444, compound

HRID 1692887Notes

Reaction equation

HRID 1692887 reaction equation
F[C@H]1[C@@H](N(C)C)CCNC1.[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([C:20]2[N:28]=[C:27]3[C:23]([N:24]=[C:25]([CH2:30][N:31]4[CH2:36][CH2:35][CH:34]([N:37]([CH3:39])[CH3:38])[CH:33]([F:40])[CH2:32]4)[N:26]3[CH3:29])=[C:22]([N:41]3[CH2:46][CH2:45][O:44][CH2:43][CH2:42]3)[N:21]=2)=[CH:12]1>>[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([C:20]2[N:28]=[C:27]3[C:23]([N:24]=[C:25]([CH2:30][N:31]4[CH2:36][CH2:35][C@H:34]([N:37]([CH3:39])[CH3:38])[C@H:33]([F:40])[CH2:32]4)[N:26]3[CH3:29])=[C:22]([N:41]3[CH2:46][CH2:45][O:44][CH2:43][CH2:42]3)[N:21]=2)=[CH:12]1

Participants

3

Reactant 2

HCID 67279564HCID 67279564, compoundHCID 67280787HCID 67280787, compound

Product 1

HCID 59603444HCID 59603444, compound

Procedure

Following the procedures to prepare 104, racemic cis-3-fluoro-N,N-dimethylpiperidin-4-amine was converted to 1-((2-(1H-indol-3-yl)-9-methyl-6-morpholino-9H-purin-8-yl)methyl)-3-fluoro-N,N-dimethylpiperidin-4-amine. The enantiomers of the final product were separated by SFC to give 123. LCMS: M+H+=493.2. 1H-NMR (400 MHz, DMSO-d6): δ 11.5 (s, 1H), 8.61 (m, 1H), 8.13 (m, 1H), 7.42 (m, 1H), 7.14 (m, 2H), 4.27 (s, br, 4H), 3.85 (s, 3H), 3.79 (m, 6H), 3.04 (m, 1H), 2.91 (m, 1H), 2.05-2.29 (m, 5H), 1.59-1.84 (m, 2H), 1.17 (t, 1H)

Workup

  1. customThe enantiomers of the final product were separated by SFC

Sources & evidence

ORD record
ord-26fc67093b054e66a7c411bb181b5601
Source dataset
uspto-grants-2012_04
Patent number
US08158625B2

Reaction notes

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