Triethylamine → HCID 86689153, compound

HRID 1752469Notes

Reaction equation

HRID 1752469 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C@:8]2([CH2:17][CH2:18][O:19][CH3:20])[C:13]([F:15])([F:14])[CH2:12][O:11][C:10]([NH2:16])=[N:9]2)[C:5]([F:21])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:29][O:30][C:31]1[CH:52]=[CH:51][C:34]([C:35](Cl)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=2)=[CH:33][CH:32]=1>ClCCl>[CH3:43][O:42][C:39]1[CH:38]=[CH:37][C:36]([C:35]([NH:16][C:10]2[O:11][CH2:12][C:13]([F:15])([F:14])[C@:8]([C:6]3[C:5]([F:21])=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=3)([CH2:17][CH2:18][O:19][CH3:20])[N:9]=2)([C:34]2[CH:33]=[CH:32][C:31]([O:30][CH3:29])=[CH:52][CH:51]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH:41][CH:40]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 86689154HCID 86689154, compound

Product 1

HCID 86689153HCID 86689153, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-4-(6-bromo-3-fluoro-pyridin-2-yl)-5,5-difluoro-4-(2-methoxy-ethyl)-5,6-dihydro-4H-[1,3]oxazin-2-ylamine (200 mg, 0.543 mmol) and triethylamine (110 mg, 1.087 mmol) in dichloromethane (5.4 ml) was added solid 4,4′-dimethoxytrityl chloride (202 mg, 0.598 mmol) under argon atmosphere. The green solution was stirred at rt for 16 hrs and was then evaporated in vacuo. The crude product was taken up with ethyl acetate and washed with aqueous citric acid, aqueous sodium bicarbonate solution, water and brine. The organic phase was dried over sodium sulfate, filtered and evaporated. The crude product (380 mg) was chromatographed over silica gel (Redisep column 12 g, cyclohexane/ethyl acetate 8:2) to give the title compound as a colourless foam. 339 mg (93% yield).

Workup

  1. customwas then evaporated in vacuo
  2. washwashed with aqueous citric acid, aqueous sodium bicarbonate solution, water and brine
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product (380 mg) was chromatographed over silica gel (Redisep column 12 g, cyclohexane/ethyl acetate 8:2)

Sources & evidence

ORD record
ord-1eebde6678a6452dbfaa24c177ce3e18
Source dataset
uspto-grants-2015_10
Patent number
US09163011B2

Reaction notes

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