Bromoacetic Acid → HCID 135774142, compound

HRID 720147Notes

Reaction equation

HRID 720147 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]2[C:15](=[O:16])[NH:14][N:13]=[CH:12][C:7]3=[CH:8][NH:9][C:10]([CH:11]=1)=[C:6]23.Br[CH2:18][C:19]([OH:21])=O.F[P-](F)(F)(F)(F)F.[N:29]1([O:38]C(N(C)C)=[N+](C)C)[C:33]2[N:34]=[CH:35][CH:36]=[CH:37][C:32]=2[N:31]=[N:30]1.C(N(CC)CC)C>CN(C)C=O>[O:16]=[C:15]1[C:5]2[C:6]3[C:7](=[CH:8][NH:9][C:10]=3[CH:11]=[C:3]([NH:2][C:19](=[O:21])[CH2:18][O:38][N:29]3[C:33]4=[N:34][CH:35]=[CH:36][CH:37]=[C:32]4[N:31]=[N:30]3)[CH:4]=2)[CH:12]=[N:13][NH:14]1

Participants

6

Reactant 4

HCID 6227Bromoacetic AcidHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 135774127HCID 135774127, compound

Product 1

HCID 135774142HCID 135774142, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a manner analogous to that of Example 19, to a stirred suspension of 8-amino-1,5-dihydro-6H-[1,2]diazepino[4,5,6-cd]indol-6-one hydrochloride in anhydrous N,N-dimethylformamide (9 mL) was added bromoacetic acid (168 mg. 1.2 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (553 mg, 1.4 mmol) and triethylamine. The reaction was stirred at room temperature for 16 hours. The volatile components were evaporated and water was added to the residue. The precipitated orange solids were collected by filtration and washed with water and ethyl acetate. After drying, the title compound (158 mg) was obtained as an orange powder in 35% yield.

Workup

  1. customThe volatile components were evaporated
  2. additionwater was added to the residue
  3. filtrationThe precipitated orange solids were collected by filtration
  4. washwashed with water and ethyl acetate
  5. customAfter drying

Sources & evidence

ORD record
ord-1af5e875875243e5a4f75392438979d4
Source dataset
uspto-grants-2006_11
Patent number
US07132533B2

Reaction notes

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