Triphenylphosphine → HCID 57794622, compound

HRID 2099801Notes

Reaction equation

HRID 2099801 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[N:8]([CH:13]1[CH2:18][CH2:17][N:16]([C:19]([NH:21][CH:22]([C:34]3[NH:38][N:37]=[N:36][N:35]=3)[CH2:23][C:24]3[CH:25]=[C:26]4[C:30](=[C:31]([CH3:33])[CH:32]=3)[NH:29][N:28]=[CH:27]4)=[O:20])[CH2:15][CH2:14]1)[CH2:7]2.O[CH2:40][CH:41]1[CH2:46][CH2:45][N:44]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:43][CH2:42]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[C:50]([O:49][C:47]([N:44]1[CH2:45][CH2:46][CH:41]([CH2:40][N:35]2[C:34]([CH:22]([NH:21][C:19]([N:16]3[CH2:15][CH2:14][CH:13]([N:8]4[CH2:7][C:6]5[C:11](=[C:2]([F:1])[CH:3]=[CH:4][CH:5]=5)[NH:10][C:9]4=[O:12])[CH2:18][CH2:17]3)=[O:20])[CH2:23][C:24]3[CH:25]=[C:26]4[C:30](=[C:31]([CH3:33])[CH:32]=3)[NH:29][N:28]=[CH:27]4)=[N:38][N:37]=[N:36]2)[CH2:42][CH2:43]1)=[O:48])([CH3:53])([CH3:51])[CH3:52]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 5462977Diethyl azodicarboxylateHCID 178425596HCID 178425596, compound

Product 1

HCID 57794622HCID 57794622, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-(8-fluoro-2-oxo-1,2-dihydroquinazolin-3[4H]-yl)-N-(2{7-methyl-1H-indazol-5-yl}-1-{1H-tetrazol-5-yl}ethyl)piperidin-1-carboxamide (50 mg, 0.1 mmol) and tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (22 mg, 0.11 mmol) in dry tetrahydrofuran (3.0 mL) at 0° C. was added in one portion triphenylphosphine (27.5 mg, 0.11 mmol) followed by a dropwise addition of diethylazodicarboxylate (10 μL, 0.105 mmol). The resulting mixture was stirred briefly at 0° C. and then allowed to warm to room temperature. After 16 h, the solvent was removed and the residue purified by column chromatography to afford tert-butyl-4-({5-(1-[4-(8-fluoro-2-oxo-1,2-dihydroquinazolin-3 [4H]-yl)piperidine-1-carboxamido]-2-(7-methyl-1H-indazol-5-yl)ethyl)-1H-tetrazol-1-yl}methyl)piperidine-1-carboxylate. MS: tR=1.44 min, 716.17 (MH)+ and tert-butyl-4-({5-(1-[4-(8-fluoro-2-oxo-1,2-dihydroquinazolin-3[4H]-yl)piperidine-1-carboxamido]-2-(7-methyl-1H-indazol-5-yl)ethyl)-2H-tetrazol-1-yl}methyl)piperidine-1-carboxylate. MS: tR=1.45 min, 716.16 (MH)+.

Workup

  1. temperatureto warm to room temperature
  2. customthe solvent was removed
  3. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-e41a33722d504e1eadc4881440aed1cd
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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