6-chloro-1H-pyrazolo[3,4-d]pyrimidine → 4-(3-((6-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-2,4,5-trifluorophenyl)morpholine

HRID 577293Notes

Reaction equation

HRID 577293 reaction equation
Br[CH2:2][C:3]1[C:4]([F:17])=[C:5]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:6]=[C:7]([F:10])[C:8]=1[F:9].[Cl:18][C:19]1[N:24]=[C:23]2[NH:25][N:26]=[CH:27][C:22]2=[CH:21][N:20]=1>>[Cl:18][C:19]1[N:24]=[C:23]2[N:25]([CH2:2][C:3]3[C:4]([F:17])=[C:5]([N:11]4[CH2:16][CH2:15][O:14][CH2:13][CH2:12]4)[CH:6]=[C:7]([F:10])[C:8]=3[F:9])[N:26]=[CH:27][C:22]2=[CH:21][N:20]=1

Participants

3

Reactant 2

HCID 529112546-chloro-1H-pyrazolo[3,4-d]pyrimidineHCID 86671750HCID 86671750, compound

Product 1

HCID 866717494-(3-((6-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-2,4,5-trifluorophenyl)morpholine

Procedure

4-(3-(bromomethyl)-2,4,5-trifluorophenyl)morpholine and 6-chloro-1H-pyrazolo[3,4-d]pyrimidine were coupled as in Procedure D (Step ii) to afford 4-(3-((6-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-2,4,5-trifluorophenyl)morpholine followed by Procedure D (Step i) using tert-butyl 4-amino-1H-pyrazole-1-carboxylate to afford the title product. 1H NMR (d6-DMSO) δ 12.55 (s, 1H), 9.87 (br s, 1H), 8.89 (s, 1H), 8.15 (br s, 1H), 8.00 (s, 1H), 7.70 (s, 1H), 7.21-7.14 (m, 1H), 5.58 (s, 2H), 3.68 (t, 4H), 2.93 (t, 4H); LC-MS method B, (ES+) 431.1, RT=7.59 min.

Sources & evidence

ORD record
ord-b8712fc7111d460dae8adfcf92fafeb7
Source dataset
uspto-grants-2015_05
Patent number
US09040545B2

Reaction notes

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