Diisopropylethylamine → 2-(S)-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid [5-(1-ethyl-pentyl)-[1,3,4]thiadiazol-2-yl]-amide

HRID 1767033Notes

Reaction equation

HRID 1767033 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[CH2:8][CH:7]([NH:13][CH:14]([CH2:18][CH2:19][CH3:20])[C:15]([OH:17])=O)[CH2:6][CH2:5]2.[CH2:21]([CH:23]([C:28]1[S:32][C:31]([NH2:33])=[N:30][N:29]=1)[CH2:24][CH2:25][CH2:26][CH3:27])[CH3:22].F[B-](F)(F)F.O=C1C=CC=CN1OC(N(C)C)=[N+](C)C.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH2:21]([CH:23]([C:28]1[S:32][C:31]([NH:33][C:15](=[O:17])[C@@H:14]([NH:13][CH:7]2[CH2:6][CH2:5][C:4]3[C:9](=[C:10]([F:12])[CH:11]=[C:2]([F:1])[CH:3]=3)[CH2:8]2)[CH2:18][CH2:19][CH3:20])=[N:30][N:29]=1)[CH2:24][CH2:25][CH2:26][CH3:27])[CH3:22]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 28491875-(1-Ethylpentyl)-1,3,4-thiadiazol-2-amineHCID 211128022-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid

Product 1

HCID 115255422-(S)-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid [5-(1-ethyl-pentyl)-[1,3,4]thiadiazol-2-yl]-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid (28 mg), 5-(1-ethyl-pentyl)-[1,3,4]thiadiazol-2-ylamine (20 mg), O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (30 mg), diisopropylethylamine (0.04 ml) in DMF (1 ml) was shaked in shaker overnight. The mixture was quenched with water, basified with satuated sodium bicarbonate, and extracted twice with ethyl acetate. The organic layer was separated, dried over sodium sulfate, and concentrated to give the crude material. The crude material was purified by biotage silica gel column chromatography using methylene chloride to 3% methanol in methylene chloride to give the title compound as a glass foam. LC-MS RT=2.5 min, M+1=465.0, M−1=463.2. The corresponding HCl salt was prepared as an off-white solid.

Workup

  1. customwas shaked in shaker overnight
  2. customThe mixture was quenched with water
  3. extractionextracted twice with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto give the crude material
  8. customThe crude material was purified by biotage silica gel column chromatography

Sources & evidence

ORD record
ord-861425e9a118465d844cee60861cae6a
Source dataset
uspto-grants-2007_06
Patent number
US07232820B2

Reaction notes

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