1-Hydroxybenzotriazole → HCID 59042568, compound

HRID 2414327Notes

Reaction equation

HRID 2414327 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[CH2:17][O:16][C:15]3=[O:24])[CH2:10][CH2:9]2)=[C:4]([Cl:25])[CH:3]=1.[CH3:26][N:27]1[CH2:34][CH2:33][CH2:32][C@H:28]1[C:29](O)=[O:30].C(N(CC)C(C)C)(C)C.ON1C2C=CC=CC=2N=N1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[Cl:25][C:4]1[CH:3]=[C:2]([NH:1][C:29]([C@@H:28]2[CH2:32][CH2:33][CH2:34][N:27]2[CH3:26])=[O:30])[CH:7]=[CH:6][C:5]=1[N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[CH2:17][O:16][C:15]2=[O:24])[CH2:12][CH2:13]1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 643474N-Methyl-L-prolineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 226446801-[1-(4-Amino-2-chlorophenyl)piperidin-4-yl]-1,4-dihydro-2H-3,1-benzoxazin-2-one

Product 1

HCID 59042568HCID 59042568, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product from example 120 step (ii) (0.1 g), N-methyl-L-proline (0.044 g), N,N-diisopropylethylamine (0.17 ml), 1-hydroxybenzotriazole (0.043 g), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (0.103 g) in N,N-dimethylformamide (3 ml) were stirred at room temperature overnight then partitioned between ethyl acetate and water. The organic layer was washed with water, dried and evaporated under reduced pressure. Purification was by chromatography eluting with 4% methanol/dichloromethane. Yield 0.038 g.

Workup

  1. customthen partitioned between ethyl acetate and water
  2. washThe organic layer was washed with water
  3. customdried
  4. customevaporated under reduced pressure
  5. customPurification
  6. washeluting with 4% methanol/dichloromethane

Sources & evidence

ORD record
ord-2707d10fea2c40728553b62fa1bad377
Source dataset
uspto-grants-2004_11
Patent number
US06812226B2

Reaction notes

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