Diisopropylethylamine → N-(Isoquinolin-6-yl)-2,3-dihydro-1H-indole-2-carboxamide

HRID 2378333Notes

Reaction equation

HRID 2378333 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH:13]1[C:21](O)=[O:22].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH:8]1[C:9]2[C:4](=[CH:3][C:2]([NH:1][C:21]([CH:13]3[CH2:14][C:15]4[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=4)[NH:12]3)=[O:22])=[CH:11][CH:10]=2)[CH:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 86074Indoline-2-carboxylic acidHCID 5889916-AminoisoquinolineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 59857966N-(Isoquinolin-6-yl)-2,3-dihydro-1H-indole-2-carboxamideYield 6.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 6-aminoisoquinoline (25 mg, 0.17 mmol) in DMF (1.0 mL) was added indoline-2-carboxylic acid (30 mg, 0.17 mmol), HATU (70 mg, 0.19 mmol), diisopropylethylamine (35 μL, 0.19 mmol) and stirred overnight at 40° C. The reaction mixture was concentrated and purified by prep-HPLC to afford the titled compound (3.0 mg): 1H NMR (400 MHz, METHANOL-d4) δ ppm 3.18 (dd, J=16.11, 8.30 Hz, 1H) 3.56 (dd, J=16.20,10.54 Hz, 1H) 4.52 (dd, J=10.54, 8.40 Hz, 1H) 6.70-6.81 (m, 2H) 6.99-7.10 (m, 3H) 7.73 (d, J=6.05 Hz, 1H) 7.81 (dd, J=8.88, 2.05 Hz, 1H) 8.05 (d, J=8.98 Hz, 1H) 8.35 (d, J=5.86 Hz, 1H) 8.40 (d, J=1.95 Hz, 1H) 9.11 (s, 1H); LCMS: 290 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-91d35d3d4b974a39992dab02a18172ae
Source dataset
uspto-grants-2008_12
Patent number
US07470787B2

Reaction notes

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