Triethylamine → HCID 71059700, compound

HRID 1525167Notes

Reaction equation

HRID 1525167 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[S:8][CH2:7][CH2:6][C@@:5]12[C:16]([F:18])([F:17])[CH2:15][O:14][C:13]([NH2:19])=[N:12]1.C(N(CC)CC)C.[CH3:27][O:28][C:29]1[CH:50]=[CH:49][C:32]([C:33](Cl)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)=[CH:31][CH:30]=1>ClCCl>[CH3:41][O:40][C:37]1[CH:36]=[CH:35][C:34]([C:33]([C:32]2[CH:31]=[CH:30][C:29]([O:28][CH3:27])=[CH:50][CH:49]=2)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[NH:19][C:13]2[O:14][CH2:15][C:16]([F:18])([F:17])[C@:5]3([N:12]=2)[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=2)[S:8][CH2:7][CH2:6]3)=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 71059612HCID 71059612, compound2×

Product 1

HCID 71059700HCID 71059700, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-6′-bromo-5,5-difluoro-5,6-dihydro spiro[[1,3]oxazine-4,4′-thiochroman]-2-amine (intermediate B6.9) (460 mg, 1.32 mmol) and triethylamine (267 mg, 2.63 mmol) in dichloromethane (10 ml) was cooled to 0° C. and 4,4′-dimethoxytritylchloride (469 mg, 1.38 mmol) was added. The reaction mixture was left to warm to room temperature and stirred for 15 hours. For the workup, the reaction mixture was evaporated and the residue directly purified by chromatography on silica gel using a gradient of heptane/ethyl acetate=0:100 to 60:40 as the eluent. The (R)—N-(bis(4-methoxyphenyl)(phenyl)methyl)-6′-bromo-5,5-difluoro-5,6-dihydrospiro[[1,3]oxazine-4,4′-thiochroman]-2-amine (789 mg, 92% yield) was obtained as a yellow foam. MS (ISP): m/z=651.0 [M+H]+ and 353.0 [M+2+H]+.

Workup

  1. waitThe reaction mixture was left
  2. customFor the workup, the reaction mixture was evaporated
  3. customthe residue directly purified by chromatography on silica gel using a gradient of heptane/ethyl acetate=0:100 to 60:40 as the eluent

Sources & evidence

ORD record
ord-37fd72316cd846cd9d73edeb4c383a33
Source dataset
uspto-grants-2015_07
Patent number
US09079919B2

Reaction notes

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