1-Hydroxybenzotriazole → HCID 9871764, compound

HRID 373799Notes

Reaction equation

HRID 373799 reaction equation
[NH2:1][CH:2]1[C:8]2[CH:9]=[N:10][CH:11]=[N:12][C:7]=2[C:6]2[CH:13]=[CH:14][CH:15]=[CH:16][C:5]=2[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:3]1.[C:23]([NH:30][C@H:31]([C:39](O)=[O:40])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.C(N(CC)CC)C>[C:26]([O:25][C:23]([NH:30][C@@H:31]([CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:39]([NH:1][CH:2]1[C:8]2[CH:9]=[N:10][CH:11]=[N:12][C:7]=2[C:6]2[CH:13]=[CH:14][CH:15]=[CH:16][C:5]=2[C:4]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[N:3]1)=[O:40])=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19763361HCID 19763361, compound

Product 1

HCID 9871764HCID 9871764, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Crude 5(R,S)-amino-7-phenyl-5H-pyrimido[5,4-d][2]benzazepine (1.37 g), Boc-L-phenylalanine (1.37 g, 5.17 mmole), 1-hydroxybenzotriazole (HBT) (0.70 g, 5.17 mmole), and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (EDC) (0.99 g, 5.17 mmole) are combined in DMF (30 ml) and stirred at room temperature. The pH of the mixture is adjusted to 9.5 with triethylamine. After about 1/2 hour, the DMF is removed in vacuo and the residue is partitioned between methylene chloride and 10% citric acid solution. The layers are separated and the organic phase is washed with saturated NaHCO3 solution, water and brine, then dried over Na2SO4, filtered, and evaporated to dryness in vacuo. The residue is chromatographed on silica gel and the combined product fractions evaporated to dryness in vacuo to give the title compound as a mixture of diastereomers.

Workup

  1. customthe DMF is removed in vacuo
  2. customthe residue is partitioned between methylene chloride and 10% citric acid solution
  3. customThe layers are separated
  4. washthe organic phase is washed with saturated NaHCO3 solution, water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness in vacuo
  8. customThe residue is chromatographed on silica gel
  9. customthe combined product fractions evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-f4b7110c17c14c9a8bfb2fa8cb030247
Source dataset
uspto-grants-1992_11
Patent number
US05166151

Reaction notes

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