Dimethylformamide → (R)-2-(5-(2-(1-Hydroxycycloheptyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl acetate

HRID 418524Notes

Reaction equation

HRID 418524 reaction equation
[C:1]([O:4][CH2:5][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:19])[C:14]=2[NH2:18])[C:9]1=[O:20])[CH3:7])(=[O:3])[CH3:2].[OH:21][C:22]1([CH2:29][C:30](O)=[O:31])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.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.CN(C)C=O.C(Cl)Cl>>[C:1]([O:4][CH2:5][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:19])[C:14]=2[NH:18][C:30](=[O:31])[CH2:29][C:22]2([OH:21])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[C:9]1=[O:20])[CH3:7])(=[O:3])[CH3:2]

Participants

7

Reactant 6

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 545930862-(1-Hydroxycycloheptyl)acetic acidHCID 59515683(R)-2-(5-amino-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Product 1

HCID 59845716(R)-2-(5-(2-(1-Hydroxycycloheptyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Procedure

A round bottom flask was charged with (R)-2-(5-amino-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl acetate (100.00 mg, 0.36454 mmol), 2-(1-hydroxycycloheptyl)acetic acid (75.3 mg, 0.437 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (346 mg, 0.911 mmol), N,N-diisopropylethylamine (0.159 mL, 0.911 mmol), N,N-dimethylformamide (2 mL, 30 mmol) and methylene chloride (8 mL, 100 mmol). The reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was taken onto the next step without further purification.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was taken onto the next step without further purification

Sources & evidence

ORD record
ord-3666586367784effbff7798da07e2d90
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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