Water → 2-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-1,2,3-triazolo(4,5-d)pyrimidin-3-yl)tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl)oxy)ethanol

HRID 2404976Notes

Reaction equation

HRID 2404976 reaction equation
Cl[C:2]1[C:3]2[N:14]=[N:13][N:12]([C@H:15]3[C@@H:19]4[O:20][C:21]([CH3:24])([CH3:23])[O:22][C@@H:18]4[C@@H:17]([O:25][CH2:26][CH2:27][OH:28])[CH2:16]3)[C:4]=2[N:5]=[C:6]([S:8][CH2:9][CH2:10][CH3:11])[N:7]=1.[F:29][C:30]1[CH:31]=[C:32]([C@@H:37]2[CH2:39][C@H:38]2[NH2:40])[CH:33]=[CH:34][C:35]=1[F:36].C(N(CC)C(C)C)(C)C.O>ClCCl>[F:29][C:30]1[CH:31]=[C:32]([C@@H:37]2[CH2:39][C@H:38]2[NH:40][C:2]2[C:3]3[N:14]=[N:13][N:12]([C@H:15]4[C@@H:19]5[O:20][C:21]([CH3:24])([CH3:23])[O:22][C@@H:18]5[C@@H:17]([O:25][CH2:26][CH2:27][OH:28])[CH2:16]4)[C:4]=3[N:5]=[C:6]([S:8][CH2:9][CH2:10][CH3:11])[N:7]=2)[CH:33]=[CH:34][C:35]=1[F:36]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 9834068(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamineHCID 210357742-[[(3aR,4S,6R,6aS)-6-[7-Chloro-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Product 1

HCID 672892902-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-1,2,3-triazolo(4,5-d)pyrimidin-3-yl)tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl)oxy)ethanolYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-((3aR,4S,6R,6aS)-6-(7-chloro-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol (370 mg, 0.86 mmol, 1.00 equiv) (15 mL), (1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine (145.6 mg, 0.86 mmol, 1.00 equiv.) and N,N-diisopropylethylamine (155.7 mg, 1.21 mmol, 1.20 equiv.) in dichloromethane was stirred at ambient temperature for about 16 hours, and then water (10 mL) was added. Standard extractive workup with dichloromethane (3×10 mL) gave the title product as a yellow oil (450 mg; yield=93%). m/z=563 (MH)+.

Sources & evidence

ORD record
ord-50d8862d99374feeb1acbd567752a468
Source dataset
uspto-grants-2014_08
Patent number
US08802850B2

Reaction notes

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