Dichloromethane → HCID 59515734, compound

HRID 418508Notes

Reaction equation

HRID 418508 reaction equation
[C:1]([O:4][CH2:5][CH2:6][NH:7][C:8]1[C:9]([NH2:25])=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[N:13]([CH2:19][CH2:20][O:21][C:22](=[O:24])[CH3:23])[CH:12]=[CH:11]2)(=[O:3])[CH3:2].[F:26][C:27]1[C:32]([C:33]([F:36])([F:35])[F:34])=[CH:31][CH:30]=[CH:29][C:28]=1[CH2:37][C:38](O)=[O:39].F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.C(Cl)Cl>>[C:1]([O:4][CH2:5][CH2:6][NH:7][C:8]1[C:9]([NH:25][C:38](=[O:39])[CH2:37][C:28]2[CH:29]=[CH:30][CH:31]=[C:32]([C:33]([F:34])([F:35])[F:36])[C:27]=2[F:26])=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[N:13]([CH2:19][CH2:20][O:21][C:22](=[O:24])[CH3:23])[CH:12]=[CH:11]2)(=[O:3])[CH3:2]

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 27375882-Fluoro-3-(trifluoromethyl)phenylacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59515926HCID 59515926, compound

Product 1

HCID 59515734HCID 59515734, compound

Conditions

Temperature
40 °C

Procedure

A reaction vial was charged with acetic acid 2-[6-(2-acetoxy-ethylamino)-5-amino-1-oxo-1H-isoquinolin-2-yl]-ethyl ester (100.00 mg, 0.000 28788 mol), 2-(2-fluoro-3-(trifluoromethyl)phenyl)acetic acid (76.74 mg, 0.0003454 mol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (274 mg, 0.000720 mol), N,N-diisopropylethylamine (0.125 mL, 0.000720 mol) and methylene chloride (3 mL, 0.05 mol). The reaction was heated at 40° C. for 5 h. The solvent was removed under reduced pressure and the residue purified by flash chromatography to afford the product as an off white solid.

Workup

  1. customA reaction
  2. customThe solvent was removed under reduced pressure
  3. customthe residue purified by flash chromatography
  4. customto afford the product as an off white solid

Sources & evidence

ORD record
ord-965c78c69e29449498414671df6a509a
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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