(2R)-2-(Methoxymethyl)pyrrolidine → HCID 67020568, compound

HRID 550511Notes

Reaction equation

HRID 550511 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[N:11][C:12]=2[NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:23]=[N:24][C:25]([CH3:28])=[CH:26][CH:27]=3)=[C:17]([Cl:29])[CH:16]=2)[NH:7][N:6]=1.[CH3:30][O:31][CH2:32][C@H:33]1[CH2:37][CH2:36][CH2:35][NH:34]1>>[Cl:29][C:17]1[CH:16]=[C:15]([NH:14][C:12]2[N:11]=[CH:10][N:9]=[C:8]3[NH:7][N:6]=[C:5]([O:4][CH2:3][CH2:2][N:34]4[CH2:35][CH2:36][CH2:37][C@@H:33]4[CH2:32][O:31][CH3:30])[C:13]=23)[CH:20]=[CH:19][C:18]=1[O:21][C:22]1[CH:23]=[N:24][C:25]([CH3:28])=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 671216(2R)-2-(Methoxymethyl)pyrrolidineHCID 116548903-(2-chloroethoxy)-N-{3-chloro-4-[(6-methylpyridin-3-yl)oxy]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 67020568HCID 67020568, compoundYield 58%

Procedure

The procedure described in Example 23 was repeated using 3-(2-chloroethoxy)-N-{3-chloro-4-[(6-methylpyridin-3-yl)oxy]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine (prepared as described in Example 16) and (2R)-2-(methoxymethyl)pyrrolidine to give the title compound in 58% yield; NMR Spectrum: 1.43-1.49 (m, 1H), 1.61-1.70 (m, 2H), 1.81-1.87 (m, 1H), 2.32 (dd, 1H), 2.45 (s, 3H), 2.68 (m, 1H), 2.74-2.80 (m, 1H), 3.13-3.16 (m, 2H), 3.17 (s, 3H), 3.28-3.31 (m, 2H), 4.44 (t, 2H), 7.20 (d, 1H), 7.27 (br s, 2H), 7.73 (d, 1H), 8.14 (s, 1H), 8.21 (s, 1H), 8.36 (s, 1H), 8.62 (br s, 1H); Mass Spectrum: 510 (MH+).

Sources & evidence

ORD record
ord-7289647008474481bd0bc9bb8e8fbe05
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

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