Carbon Tetrachloride → HCID 16116962, compound

HRID 1162210Notes

Reaction equation

HRID 1162210 reaction equation
[CH3:1][N:2]([CH3:19])[C:3](=[O:18])[C@@H:4]([O:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[C:9](=O)[NH:10][CH:11]=[N:12]2)[CH3:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl.[N:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[CH2:50][N:51]1[C:59]2[C:54](=[CH:55][C:56]([NH2:60])=[CH:57][CH:58]=2)[CH:53]=[N:52]1>ClCCCl>[CH3:1][N:2]([CH3:19])[C:3](=[O:18])[C@@H:4]([O:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[C:9]([NH:60][C:56]1[CH:55]=[C:54]3[C:59](=[CH:58][CH:57]=1)[N:51]([CH2:50][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][N:44]=1)[N:52]=[CH:53]3)=[N:10][CH:11]=[N:12]2)[CH3:5]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 219523661-(Pyridin-2-ylmethyl)-1H-indazol-5-amineHCID 136346720HCID 136346720, compound

Product 1

HCID 16116962HCID 16116962, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of (2S)—N,N-dimethyl-2-[(4-oxo-3,4-dihydroquinazolin-5-yl)oxy]propanamide (200 mg, 0.77 mmol), triphenylphosphine (603 mg, 2.3 mmol) and carbon tetrachloride (2.2 ml, 23 mmol) in 1,2-dichloroethane (5 ml) was stirred at 45° C. for 2 hours. 1-(Pyridin-2-ylmethyl)-1H-indazol-5-amine (179 mg, 0.8 mmol) was added and the solvent was evaporated under vacuum. Acetonitrile (5 ml) was added. The mixture was stirred at 75° C. for 2 hours. After cooling, 6N methanolic ammonia (3 ml) was added. The solvents were evaporated under vacuum. The residue was purified by chromatography on silica gel (eluant: 3% to 5% methanol in DCM) to give the title compound as a white foam (208 mg, 58%); NMR Spectrum (CDCl3) 1.72 (d, 3H), 3.06 (s, 3H), 3.14 (s, 3H), 5.43 (q, 1H), 5.75 (s, 2H), 6.81 (m, 2H), 7.17 (m, 1H), 7.41 (d, 1H), 7.48 (d, 1H), 7.62-7.53 (m, 2H), 7.81 (dd, 1H), 8.10 (s, 1H), 8.44 (d, 1H), 8.58 (d, 1H), 8.62 (s, 1H); Mass spectrum 468.

Workup

  1. customthe solvent was evaporated under vacuum
  2. additionAcetonitrile (5 ml) was added
  3. stirringThe mixture was stirred at 75° C. for 2 hours
  4. temperatureAfter cooling
  5. addition6N methanolic ammonia (3 ml) was added
  6. customThe solvents were evaporated under vacuum
  7. customThe residue was purified by chromatography on silica gel (eluant: 3% to 5% methanol in DCM)

Sources & evidence

ORD record
ord-fd07503fb73344bbaa914eb7fe5da3a4
Source dataset
uspto-grants-2010_10
Patent number
US07820683B2

Reaction notes

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