Pyrrolidine → HCID 11619915, compound

HRID 550486Notes

Reaction equation

CS(O[CH2:6][CH2:7][O:8][C:9]1[C:17]2[C:12](=[N:13][CH:14]=[N:15][C:16]=2[NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=3)=[C:21]([O:34][CH3:35])[CH:20]=2)[NH:11][N:10]=1)(=O)=O.[NH:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1>>[F:33][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][CH:30]=1)[CH2:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([NH:18][C:16]2[N:15]=[CH:14][N:13]=[C:12]3[NH:11][N:10]=[C:9]([O:8][CH2:7][CH2:6][N:36]4[CH2:40][CH2:39][CH2:38][CH2:37]4)[C:17]=23)=[CH:20][C:21]=1[O:34][CH3:35]

Participants

Reactant 2

HCID 31268Pyrrolidine

HCID 11555176HCID 11555176, compound

Product 1

HCID 11619915HCID 11619915, compoundYield 30%

Procedure

The procedure described in Example 55 was repeated using 2-{[4-({4-[(3-fluorobenzyl)oxy]-3-methoxyphenyl}amino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]oxy}ethyl methanesulfonate (prepared as described in Example 22) and pyrrolidine to give the title compound in 30% yield; NMR Spectrum: 1.66 (s, 4H), 2.55 (s, 4H), 2.88 (t, 2H), 3.80 (s, 3H), 4.42 (t, 2H), 5.11 (s, 2H), 7.00 (d, 1H), 7.16 (m, 2H), 7.29 (m, 2H), 7.38 (d, 1H), 7.45 (q, 1H), 8.25 (s, 1H), 8.52 (s, 1H); Mass Spectrum: 479 (MH+).

Sources & evidence

ORD record: ord-39a98b94ee204468b8b201b4905ed698
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947676B2

Reaction notes

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