HCID 86651802, compound → HCID 69811324, compound

HRID 529094Notes

Reaction equation

HRID 529094 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([N:19]2[CH2:24][CH2:23][CH2:22][C@@:21]3([C:32]4[C:27](=[CH:28][CH:29]=[C:30]([F:33])[CH:31]=4)[N:26]([C:34]4[C:35]5[C@H:42]([CH3:43])[CH2:41][CH2:40][C:36]=5[N:37]=[CH:38][N:39]=4)[CH2:25]3)[CH2:20]2)[CH2:9][CH2:10][NH:11]C(=O)OC(C)(C)C)=[CH:4][CH:3]=1.[Cl:44][C:45]1[CH:50]=[CH:49][C:48]([C@@H:51]([N:62]2[CH2:67][CH2:66][CH2:65][C@@:64]3([C:75]4[C:70](=[CH:71][CH:72]=[C:73]([F:76])[CH:74]=4)[N:69]([C:77]4[C:78]5[C@H:85]([CH3:86])[CH2:84][CH2:83][C:79]=5[N:80]=[CH:81][N:82]=4)[CH2:68]3)[CH2:63]2)[CH2:52][CH2:53][NH:54]C(=O)OC(C)(C)C)=[CH:47][CH:46]=1>>[ClH:1].[ClH:44].[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([N:19]2[CH2:24][CH2:23][CH2:22][C@@:21]3([C:32]4[C:27](=[CH:28][CH:29]=[C:30]([F:33])[CH:31]=4)[N:26]([C:34]4[C:35]5[C@H:42]([CH3:43])[CH2:41][CH2:40][C:36]=5[N:37]=[CH:38][N:39]=4)[CH2:25]3)[CH2:20]2)[CH2:9][CH2:10][NH2:11])=[CH:6][CH:7]=1.[ClH:1].[ClH:1].[ClH:1].[Cl:44][C:45]1[CH:46]=[CH:47][C:48]([C@@H:51]([N:62]2[CH2:67][CH2:66][CH2:65][C@@:64]3([C:75]4[C:70](=[CH:71][CH:72]=[C:73]([F:76])[CH:74]=4)[N:69]([C:77]4[C:78]5[C@H:85]([CH3:86])[CH2:84][CH2:83][C:79]=5[N:80]=[CH:81][N:82]=4)[CH2:68]3)[CH2:63]2)[CH2:52][CH2:53][NH2:54])=[CH:49][CH:50]=1

Participants

4

Reactant 2

HCID 86651802HCID 86651802, compoundHCID 86651803HCID 86651803, compound

Product 2

HCID 69811324HCID 69811324, compoundHCID 86679243HCID 86679243, compound

Procedure

(R)-3-(4-chlorophenyl)-3-((R)-5-fluoro-1-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,3′-piperidine]-1′-yl)propan-1-amine trihydrochloride and (S)-3-(4-chlorophenyl)-3-((R)-5-fluoro-1-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,3′-piperidine]-1′-yl)propan-1-amine trihydrochloride were prepared by the procedures described in Example 1, Step 9, substituting (R)-tert-butyl 5-chloro-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate with tert-butyl (R)-3-(4-chlorophenyl)-3-((R)-5-fluoro-1-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,3′-piperidine]-1′-yl)propylcarbamate and tert-butyl (S)-3-(4-chlorophenyl)-3-((R)-5-fluoro-1-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,3′-piperidine]-1′-yl)propylcarbamate, respectively. Diastereomer D1: LCMS (APCI+) m/z 506, 508 [M+H]+; Rt=1.66 min. Diastereomer D2: LCMS (APCI+) m/z 506, 508 [M+H]+; Rt=1.63 min.

Sources & evidence

ORD record
ord-7eca44bfc3f54cc598c040f8d2f68496
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

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