Morpholine → HCID 11583730, compound

HRID 550504Notes

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]=[CH:29][N:28]=3)=[C:21]([CH2:33][CH3:34])[CH:20]=2)[NH:11][N:10]=1)(=O)=O.[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>>[CH2:33]([C:21]1[CH:20]=[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:35]4[CH2:40][CH2:39][O:38][CH2:37][CH2:36]4)[C:17]=23)[CH:24]=[CH:23][C:22]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)[CH3:34]

Participants

Reactant 2

HCID 8083Morpholine

HCID 11598237HCID 11598237, compound

Product 1

HCID 11583730HCID 11583730, compoundYield 45%

Procedure

The procedure described in Example 55 was repeated using 2-[(4-{[3-ethyl-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethyl methanesulfonate (prepared as described in Example 19) and morpholine to give the title compound in 45% yield; NMR Spectrum: 1.20 (t, 3H), 2.50-2.52 (m, 4H), 2.66 (q, 2H), 2.78 (t, 2H), 3.54-3.56 (m, 4H), 4.42 (t, 2H), 5.20 (s, 2H), 7.01 (d, 1H), 7.34-7.38 (m, 1H), 7.41 (d, 1H), 7.49-7.55 (m, 2H), 7.85 (td, 1H), 8.23 (s, 1H), 8.28 (s, 1H), 8.59 (d, 1H); Mass Spectrum: 476 (MH+).

Sources & evidence

ORD record: ord-efb196d2d5714ac9bcb4f15e7af877b9
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947676B2

Reaction notes

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