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Diisopropylethylamine → Methyl 3-[5-bromo-3-{[(1R,2R)-3-hydroxy-2-methyl-1-phenylpropyl]amino}-2-oxopyrazin-1(2H)-yl]-5-fluoro-4-methylbenzoate

HRID 337163
Notes
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Reaction equation

HRID 337163 reaction equation
Br[C:2]1[C:3](=[O:21])[N:4]([C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([F:20])[C:18]=2[CH3:19])[C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([Br:8])[N:7]=1.[NH2:22][C@@H:23]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C@@H:24]([CH3:27])[CH2:25][OH:26].CCN(C(C)C)C(C)C>C1COCC1.C(OCC)(=O)C>[Br:8][C:6]1[N:7]=[C:2]([NH:22][C@@H:23]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@@H:24]([CH3:27])[CH2:25][OH:26])[C:3](=[O:21])[N:4]([C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([F:20])[C:18]=2[CH3:19])[C:12]([O:14][CH3:15])=[O:13])[CH:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 12452700(2R,3R)-3-Amino-2-methyl-3-phenylpropan-1-olHCID 66689945methyl 3-(3,5-dibromo-2-oxo-1(2H)-pyrazinyl)-5-fluoro-4-methylbenzoate

Product 1

HCID 66690053Methyl 3-[5-bromo-3-{[(1R,2R)-3-hydroxy-2-methyl-1-phenylpropyl]amino}-2-oxopyrazin-1(2H)-yl]-5-fluoro-4-methylbenzoate

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To methyl 3-(3,5-dibromo-2-oxopyrazin-1(2H)-yl)-5-fluoro-4-methylbenzoate (Example 252g, 0.9 g) in THF (3 mL) was added (2R,3R)-3-amino-2-methyl-3-phenylpropan-1-ol (Example 328a, 0.389 g) and Hunig's Base (0.374 mL) and the reaction stirred at 50° C. for 8 h. The reaction mixture was diluted with ethyl acetate and washed with aqueous NaHCO3. The organics were dried (MgSO4) and concentrated in vacuo to leave the crude product which was triturated overnight in 2:1 isohexane/diethyl ether to give the subtitle compound. Purification of the filtrate (SiO2 chromatography eluting with 50-100% diethyl ether in isohexane) to give further subtitle compound (total 0.820 g).

Workup

  1. washwashed with aqueous NaHCO3
  2. dry with materialThe organics were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto leave the crude product which
  5. customwas triturated overnight in 2:1 isohexane/diethyl ether

Sources & evidence

ORD record
ord-79d9149b3c9e4c1e9a605f43826e81f2
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889692B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes