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

HRID 1773445Notes

Reaction equation

HRID 1773445 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-[[(3aS,4R,6S,6aR)-4-[7-[[(1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl]amino]-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-6-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-4b451dd1cd3a420d82a7851a307a52bd
Source dataset
uspto-grants-2016_02
Patent number
US09255104B2

Reaction notes

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