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Triphenylphosphine → N1-[4-(4-amino-1 tetrahydro-2H-4-pyranyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-methoxyphenyl]-2-fluoro-4-trifluoromethylbenzamide

HRID 897849
Notes
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Reaction equation

HRID 897849 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[NH2:13][C:14]1[N:19]=[CH:18][N:17]=[C:16]2[NH:20][N:21]=[C:22]([C:23]3[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:42])[C:31]4[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][C:32]=4[F:41])=[C:25]([O:43][CH3:44])[CH:24]=3)[C:15]=12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:64]1[CH2:69][CH2:68][CH:67](O)[CH2:66][CH2:65]1>O1CCCC1>[NH2:13][C:14]1[N:19]=[CH:18][N:17]=[C:16]2[N:20]([CH:67]3[CH2:68][CH2:69][O:64][CH2:65][CH2:66]3)[N:21]=[C:22]([C:23]3[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:42])[C:31]4[CH:36]=[CH:35][C:34]([C:37]([F:39])([F:40])[F:38])=[CH:33][C:32]=4[F:41])=[C:25]([O:43][CH3:44])[CH:24]=3)[C:15]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 74956Tetrahydro-4H-pyran-4-ol2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 178488248HCID 178488248, compound

Product 1

HCID 20817390N1-[4-(4-amino-1 tetrahydro-2H-4-pyranyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-methoxyphenyl]-2-fluoro-4-trifluoromethylbenzamide
Yield 27.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (0.07 mL, 0.45 mmol) was added into a mixture of N1-[4-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-methoxyphenyl]-2-fluoro-4-trifluoromethylbenzamide (0.10 g, 0.22 mmol), triphenylphosphine (0.12 g, 0.45 mmol) and tetrahydro-4H-pyran-4-ol (0.04 g, 0.34 mmol) in tetrahydrofuran (5 mL) and the mixture was stirred at ambient temperature overnight. Tetrahydro-4H-pyran-4-ol (0.01 g, 0.11 mmol), triphenylphosphine (0.04 g, 0.15 mmol) and diethyl azodicarboxylate (0.02 mL, 0.15 mmol) were added and the mixture was stirred at ambient temperature for 5 hours. The solvents were evaporated and the residue was purified by preparative HPLC to yield N1-[4-(4-amino-1-tetrahydro-2H-4-pyranyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-methoxyphenyl]-2-fluoro-4-trifluoromethylbenzamide (0.03 g, 0.06 mmol) as a white solid: 1H NMR (DMSO-d6 400 MHz) (9.91 (dd, 1H), 8.30(d, 1H), 8.25 (s, 1H), 8.00 (t, 1H), 7.89 (d, 1H), 7.75 (d, 1H), 7.34 (s, 1H), 7.31 (d, 1H), 6.90 (br, 2H), 4.95 (m, 1H), 4.02 (m, 2H), 3.95 (s, 3H), 3.56 (t, 2H), 2.22 (m, 2H), 1.89 (m, 2H);

Workup

  1. stirringthe mixture was stirred at ambient temperature for 5 hours
  2. customThe solvents were evaporated
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-a847397345c247ca86e9a6ad527a99b8
Source dataset
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06921763B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes