1-Hydroxybenzotriazole → 2-(6-bromo-1,2-benzisoxazol-3-yl)-N-(2-hydroxyethyl)acetamide

HRID 1988893Notes

Reaction equation

HRID 1988893 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]2[C:6]([CH2:9][C:10]([OH:12])=O)=[N:7][O:8][C:4]=2[CH:3]=1.CN(C(O[N:23]1N=N[C:25]2C=CC=N[C:24]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[OH:39]N1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>O1CCCC1>[Br:1][C:2]1[CH:14]=[CH:13][C:5]2[C:6]([CH2:9][C:10]([NH:23][CH2:24][CH2:25][OH:39])=[O:12])=[N:7][O:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 591273762-(6-Bromo-1,2-benzoxazol-3-yl)acetic acid2×

Product 1

HCID 586564962-(6-bromo-1,2-benzisoxazol-3-yl)-N-(2-hydroxyethyl)acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of (6-bromo-1,2-benzisoxazol-3-yl)acetic acid (Intermediate 32) (0.10 g) and HATU (0.18 g) in tetrahydrofuran (5 ml) was stirred at room temp. for 10 min then treated with 1-hydroxybenzotriazole (0.05 g) 2-aminoethanol (0.03 ml) and diisopropylethylamine (0.2 ml). The mixture was stirred for a further 18 h then concentrated under vacuum. The residue was partitioned between dichloromethane (5 ml) and 2M aqueous sodium carbonate (5 ml). The organic layer was dried using a hydrophobic filter tube then applied to a Varian Bond-Elut SPE cartridge. Sequential elution with dichloromethane, ether, ethyl acetate, acetonitrile and acetone yieldded the title compound as a white solid (0.08 g).

Workup

  1. stirringThe mixture was stirred for a further 18 h
  2. concentrationthen concentrated under vacuum
  3. customThe residue was partitioned between dichloromethane (5 ml) and 2M aqueous sodium carbonate (5 ml)
  4. customThe organic layer was dried
  5. washSequential elution with dichloromethane, ether, ethyl acetate, acetonitrile and acetone

Sources & evidence

ORD record
ord-2a15222a0f3b407682fb33e2513c9c2a
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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