4,7-Dichloroquinazoline → 4-(4-Chloro-phenyl)-1-[(3S,4S)-1-(7-chloro-quinazolin-4-yl)-4-hydroxy-pyrrolidin-3-yl]-piperidin-4-ol

HRID 1361503Notes

Reaction equation

HRID 1361503 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:20])[CH2:13][CH2:12][N:11]([CH:14]3[CH:18]([OH:19])[CH2:17][NH:16][CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl[C:22]1[C:31]2[C:26](=[CH:27][C:28]([Cl:32])=[CH:29][CH:30]=2)[N:25]=[CH:24][N:23]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:20])[CH2:13][CH2:12][N:11]([C@@H:14]3[C@@H:18]([OH:19])[CH2:17][N:16]([C:22]4[C:31]5[C:26](=[CH:27][C:28]([Cl:32])=[CH:29][CH:30]=5)[N:25]=[CH:24][N:23]=4)[CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2418814,7-DichloroquinazolineHCID 669679644-(4-Chlorophenyl)-1-(4-hydroxy-pyrrolidin-3-yl)-piperidin-4-ol

Product 1

HCID 584511114-(4-Chloro-phenyl)-1-[(3S,4S)-1-(7-chloro-quinazolin-4-yl)-4-hydroxy-pyrrolidin-3-yl]-piperidin-4-ol

Procedure

The title compound was prepared following general procedures described above from 4-(4-Chlorophenyl)-1-(4-hydroxy-pyrrolidin-3-yl)-piperidin-4-ol and 4,7-dichloroquinazoline. 1H-NMR (300 MHz, DMSO): δ1.57 (2 H, m), 1.90 (2 H, m), 2.60-2.70 (3 H, m), 2.96 (2 H, m), 3.70 (1 H, m), 3.85 (1 H, m), 4.10 (2 H, m), 4.36 (1 H, m), 4.90 (1 H, s), 5.32 (1 H, d), 7.40 (4 H, dd), 7.48 (1 H, m), 7.73 (1 H, d), 8.30 (1 H, d), 8.45 (1 H, s). Retention Time (LC, method, AA standard): 1.48 min. MS (M+H+): 459.

Workup

  1. custom1.48 min

Sources & evidence

ORD record
ord-e46bead5292f4b8e89017948c7bbe2d2
Source dataset
uspto-grants-2011_02
Patent number
US07880002B2

Reaction notes

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