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Tetrahydrofuran → HCID 21897866, compound

HRID 1958393
Notes
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Reaction equation

HRID 1958393 reaction equation
[H-].[Na+].[CH:3]([O:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15][CH2:14]2)=[N:11][CH:12]=1)([CH3:5])[CH3:4].C1COCC1.Cl[C:26]1[N:31]=[CH:30][N:29]=[C:28]2[N:32]([C:35]3[CH:40]=[CH:39][C:38]([S:41]([CH3:44])(=[O:43])=[O:42])=[CH:37][C:36]=3[F:45])[N:33]=[CH:34][C:27]=12>C(Cl)Cl>[F:45][C:36]1[CH:37]=[C:38]([S:41]([CH3:44])(=[O:42])=[O:43])[CH:39]=[CH:40][C:35]=1[N:32]1[C:28]2=[N:29][CH:30]=[N:31][C:26]([O:19][CH:16]3[CH2:15][CH2:14][N:13]([C:10]4[CH:9]=[CH:8][C:7]([O:6][CH:3]([CH3:5])[CH3:4])=[CH:12][N:11]=4)[CH2:18][CH2:17]3)=[C:27]2[CH:34]=[N:33]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 218976614-Chloro-1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidineHCID 218977941-{5-[(Propan-2-yl)oxy]pyridin-2-yl}piperidin-4-ol

Product 1

HCID 21897866HCID 21897866, compound

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

In a 50 mL round-bottomed flask equipped with a N2 inlet septum was placed a stir bar, NaH (60% in mineral oil, 364 mg, 0.91 mmol) and 5′-isopropoxy-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-ol (215 mg, 0.91 mmol). THF (anhydrous, 3 mL) was added to the mixture. The resulting suspension was stirred about 30 min at room temperature. 4-Chloro-1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidine (297 mg, 0.91 mmol) was then added in one portion. The mixture was stirred overnight under N2 at room temperature and the resulting slurry turned slightly yellowish. The slurry was added CH2Cl2 and filtered. The filtrate was concentrated under vacuum to give the crude product. Purification by preparative HPLC gave the desired product as an off-white solid. 1H NMR (CDCl3, 400 MHz) δ 1.36 (d, 6H), 2.17 (m, 2H), 2.30 (m, 2H), 3.13 (s, 3H), 3.74 (m, 2H), 3.97 (m, 2H), 4.50 (m, 1H), 5.76 (m, 1H), 7.04 (d, 1H), 7.60 (m, 1H), 7.87 (m, 1H), 7.94 (m, 3H), 8.34 (s, 1H), 8.64 (s, 1H). Exact mass calculated for C26H28FN5O4S 525.18, found 526.2 (MH+)

Workup

  1. customIn a 50 mL round-bottomed flask equipped with a N2 inlet septum
  2. stirringThe mixture was stirred overnight under N2 at room temperature
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under vacuum
  5. customto give the crude product
  6. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-866e7fea73e24b279582c7902238ebba
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08410119B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes