Methanol → HCID 59515657, compound

HRID 1161272Notes

Reaction equation

HRID 1161272 reaction equation
C([O:4][CH2:5][C:6]([N:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[NH2:19])[C:10]1=[O:20])([CH3:8])[CH3:7])(=O)C.C(Cl)Cl.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32](O)=[O:33])=[CH:27][C:26]=1[C:35]([F:38])([F:37])[F:36].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.CO.C(=O)([O-])[O-].[K+].[K+]>>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32]([NH:19][C:15]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:16]=2[CH:17]=[CH:18][N:9]([C:6]([CH3:7])([CH3:8])[CH2:5][OH:4])[C:10]3=[O:20])=[O:33])=[CH:27][C:26]=1[C:35]([F:36])([F:37])[F:38]

Participants

8

Reactant 7

HCID 887MethanolHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 35198824-Chloro-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 59515710HCID 59515710, compound

Product 1

HCID 59515657HCID 59515657, compound

Procedure

To a solution of 2-(5-amino-1-oxoisoquinolin-2(1H)-yl)-2-methylpropyl acetate (90.0 mg, 0.000328 mol) in methylene chloride (2 mL, 0.03 mol) were added 2-(4-chloro-3-(trifluoromethyl)phenyl)acetic acid (120 mg, 0.00049 mol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (310 mg, 0.00082 mol) and N,N-diisopropylethylamine (300 μL, 0.002 mol). The reaction mixture was stirred overnight at room temperature. The mixture was then purified by HPLC. The combined pure fractions were concentrated in vacuo and taken up in methanol (2 mL, 0.06 mol). Potassium carbonate (136 mg, 0.000984 mol) was added and the mixture was stirred at room temperature for one hour. This was followed by purification using HPLC thus producing the title compound. 1H-NMR (400 MHz, DMSO-d6) δ 10.06 (s, 1H), 8.06 (d, 1H, J=8.09 Hz), 7.88 (d, 1H, J=1.06 Hz), 7.77 (dd, 1H, J=7.79 Hz), 7.73-7.67 (m, 2H), 7.51 (d, 1H, J=8.16 Hz), 7.40 (t, 1H, J=7.91 Hz), 6.56 (d, 1H, J=8.14 Hz), 4.99 (t, 1H, J=5.64 Hz), 3.91 (s, 2H), 3.88 (d, 2H, J=5.69 Hz), 1.57 (s, 6H).

Workup

  1. customThe mixture was then purified by HPLC
  2. concentrationThe combined pure fractions were concentrated in vacuo
  3. stirringthe mixture was stirred at room temperature for one hour
  4. customThis was followed by purification

Sources & evidence

ORD record
ord-8040981f3a7b4a6783dc613111f2a60b
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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