Triethylamine → HCID 178476959, compound

HRID 1525333Notes

Reaction equation

HRID 1525333 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:11][C:12]([C:14]2[C:15]([OH:26])=[N:16][C:17]([C:20]3[N:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[N:18][CH:19]=2)=[O:13])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[CH2:27]([O:29][P:30]([O-:34])[O:31][CH2:32][CH3:33])[CH3:28].CCN(CC)CC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:26][C:15]1[C:14]([C:12]([NH:11][C:8]([C:5]2[CH:6]=[CH:7][C:2]([P:30](=[O:34])([O:31][CH2:32][CH3:33])[O:29][CH2:27][CH3:28])=[CH:3][CH:4]=2)([CH3:10])[CH3:9])=[O:13])=[CH:19][N:18]=[C:17]([C:20]2[N:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[N:16]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 3780918DiethylphosphiteHCID 178457728HCID 178457728, compound

Product 1

HCID 178476959HCID 178476959, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of N-(2-(4-bromophenyl)propan-2-yl)-4-hydroxy-2-(pyridazin-3-yl)pyrimidine-5-carboxamide (36-c, 200 mg, 0.484 mmol), diethylphosphite (195 mg, 1.45 mmol), Et3N (146 mg, 1.45 mmol) and Pd (PPh3)4 (0.1 g) in toluene (10 mL) was refluxed overnight. The reaction mixture was concentrated in vacuum. The residue was purified by pre-HPLC to afford the product 36-d, (3.0 mg). 1H NMR (300 MHz, DMSO) δ10.85 (s, 1H), 9.08 (s, 1H), 8.75 (d, J=8.4 Hz), 7.86 (m, 1H), 7.61-7.52 (m, 2H), 7.43-7.42 (m, 2H), 4.00-3.92 (m, 4H), 1.61 (s, 6H), 1.20 (t, J=6.9 Hz, 6H). LC-MS: (M+H)+ 472.

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThe reaction mixture was concentrated in vacuum
  3. customThe residue was purified by pre-HPLC
  4. customto afford the product 36-d, (3.0 mg)

Sources & evidence

ORD record
ord-ad98f37461ef4dd19603384ba39b9730
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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