1-Hydroxybenzotriazole → HCID 46852756, compound

HRID 1402751Notes

Reaction equation

HRID 1402751 reaction equation
[OH:1][C:2]([C:5]1[N:10]=[CH:9][C:8]([C:11]([O-:13])=O)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[Li+].C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:49]1[CH2:52][CH:51]([C:53]([N:55]2[CH2:61][CH2:60][CH2:59][N:58]([CH:62]3[CH2:65][CH2:64][CH2:63]3)[CH2:57][CH2:56]2)=[O:54])[CH2:50]1>CN(C=O)C>[CH:62]1([N:58]2[CH2:59][CH2:60][CH2:61][N:55]([C:53]([CH:51]3[CH2:50][N:49]([C:11]([C:8]4[CH:7]=[CH:6][C:5]([C:2]([OH:1])([CH3:3])[CH3:4])=[N:10][CH:9]=4)=[O:13])[CH2:52]3)=[O:54])[CH2:56][CH2:57]2)[CH2:65][CH2:64][CH2:63]1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 667393581-(Azetidin-3-ylcarbonyl)-4-cyclobutyl-1,4-diazepaneHCID 66739710HCID 66739710, compound

Product 1

HCID 46852756HCID 46852756, compoundYield 1.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of lithium 6-(1-hydroxy-1-methylethyl)pyridine-3-carboxylate (50 mg, 0.28 mmol) and HOBt (42 mg, 0.30 mmol) in DMF (2 mL) was added HBTU, (117 mg, 0.30 mmol) and 1-(azetidin-3-ylcarbonyl)-4-cyclobutyl-1,4-diazepane (46 mg, 0.30 mmol). After 20 hours the reaction was absorbed onto an SCX column and the product eluted with 7M NH3. Volatiles were removed at reduced pressure to give the title compound (1.4 mg, 1.2%) after purification by silica FCC (eluting with 90:9:1 Et2O/MeOH/NH3).

Workup

  1. customAfter 20 hours the reaction was absorbed onto an SCX column
  2. washthe product eluted with 7M NH3
  3. customVolatiles were removed at reduced pressure

Sources & evidence

ORD record
ord-cbed1538f7814f8fa9399d76dbcc2a2e
Source dataset
uspto-grants-2014_12
Patent number
US08912176B2

Reaction notes

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