Water → HCID 69932045, compound

HRID 869694Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[N:5]2[N:15]=[C:16]([C:18]3[C:27]([CH3:28])=[N:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)[CH:17]=[C:4]2[N:3]=1.[OH:29][C@H:30]1[CH2:34][CH2:33][NH:32][CH2:31]1.O>CN1CCCC1=O>[CH3:28][C:27]1[C:18]([C:16]2[CH:17]=[C:4]3[N:3]=[C:2]([N:32]4[CH2:33][CH2:34][CH:30]([OH:29])[CH2:31]4)[CH:7]=[C:6]([NH:8][CH:9]4[CH2:14][CH2:13][O:12][CH2:11][CH2:10]4)[N:5]3[N:15]=2)=[N:19][C:20]2[C:25]([N:26]=1)=[CH:24][CH:23]=[CH:22][CH:21]=2

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 5-chloro-2-(3-methylquinoxalin-2-yl)-N-(tetrahydro-2H-pyran-4-yl)pyrazolo[1,5-a]pyrimidin-7-amine (Example 1.001 (g)) (398 mg, 1.01 mmol) and (s)-3-hydroxypyrrolidine (351 mg, 4.03 mmol) in N-methyl-2-pyrrolidinone (5.0 mL) was heated at 80° C. for 6 h. Then the reaction mixture was poured into cold water. The resulting precipitate was collected and purified by silica gel column chromatography (ethyl acetate to ethyl acetate:methanol=7:3) to give 1-[2-(3-methylquinoxalin-2-yl)-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-3-ol (the compound of Example 1.007 listed in the Table of Examples as described hereinafter). 1H-NMR (500 MHz, CDCl3): δ 1.74-1.81 (2H, m), 2.12-2.22 (4H, m), 3.03 (3H, s), 3.58 (2H, dt, J=2.3, 11.9 Hz), 3.65-3.76 (5H, m), 4.08 (2H, dt, J=11.6, 3.2 Hz), 4.64-4.67 (1H, m), 5.16 (1H, s), 6.16 (1H, d, J=8.0 Hz), 6.66 (1H, s), 7.70-7.76 (2H, m), 8.03-8.05 (1H, m), 8.17-8.19 (1H, m).

Workup

customThe resulting precipitate was collected
custompurified by silica gel column chromatography (ethyl acetate to ethyl acetate:methanol=7:3)

Sources & evidence

ORD record: ord-7e3f309a46ce4f0bae16119f2beedf7c
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969376B2

Reaction notes

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