Dimethylformamide → HCID 24803885, compound

HRID 1624978Notes

Reaction equation

HRID 1624978 reaction equation
[O:1]=[C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:12]([OH:14])=O)[C:6]=2[CH:5]=[CH:4][NH:3]1.[C:15]12([CH2:25][NH2:26])[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH2:16]1)[CH2:22]2.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.CN(C)C=O>>[C:15]12([CH2:25][NH:26][C:12]([C:7]3[C:6]4[CH:5]=[CH:4][NH:3][C:2](=[O:1])[C:11]=4[CH:10]=[CH:9][CH:8]=3)=[O:14])[CH2:22][CH:21]3[CH2:20][CH:19]([CH2:18][CH:17]([CH2:23]3)[CH2:16]1)[CH2:24]2

Participants

7

Reactant 6

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 401520381-Oxo-1,2-dihydroisoquinoline-5-carboxylic acid

Product 1

HCID 24803885HCID 24803885, compound

Procedure

A mixture of 1,2-dihydro-1-oxoisoquinoline-5-carboxylic acid (0.107 g, 0.000566 mol), 1-adamantanemethylamine (0.120 mL, 0.000679 mol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.141 g, 0.000735 mol), 1-hydroxybenzotriazole (0.099 g, 0.00074 mol) and triethylamine (0.12 mL, 0.00085 mol) in N,N-dimethylformamide (2 mL, 0.02 mol) was stirred at room temperature for 18 hours. The mixture was poured onto water (100 ml) and extracted with ethyl acetate (3×100 ml). The combined extracts were dried over sodium sulfate and reduced in vacuo to afford the title compound.

Workup

  1. additionThe mixture was poured onto water (100 ml)
  2. extractionextracted with ethyl acetate (3×100 ml)
  3. dry with materialThe combined extracts were dried over sodium sulfate

Sources & evidence

ORD record
ord-d92496f1d33e48a38aa3775b9ad1a812
Source dataset
uspto-grants-2014_07
Patent number
US08779144B2

Reaction notes

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