Water → HCID 86671373, compound

HRID 2404398Notes

Reaction equation

HRID 2404398 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[C:7]2[Cl:12].N1[CH:18]=[CH:17]C=CC=1.ClC(O[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=O.C([N:32]([CH2:36]C)[CH:33]([CH3:35])[CH3:34])(C)C.[OH2:38]>C(#N)C>[Cl:12][C:7]1[C:8]2[C:3](=[C:2]([NH:1][C:36]([NH:32][C@@H:33]3[CH2:34][CH2:18][C@H:17]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH2:35]3)=[O:38])[CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][N:6]=1

Participants

7

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 15891Phenyl chloroformateHCID 81531DiisopropylethylamineHCID 4597715-Amino-1-chloroisoquinoline

Product 1

HCID 86671373HCID 86671373, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-amino-1-chloroisoquinoline (1.00 g, 5.60 mmol) in acetonitrile (25 mL) at room temperature was added pyridine (0.14 mL, 1.7 mmol) followed by phenyl chloroformate (0.70 mL, 5.6 mmol). After 15 minutes, Example 1E (0.903 g, 5.60 mmol) and N,N-diisopropylethylamine (3.9 mL, 22.4 mmol) were added and stirring continued for 15 minutes, followed by the addition of water. The solid was collected by filtration, washed with water then ether, and dried in a vacuum oven at 50° C. to provide the title compound (1.53 g, 75%). 1H NMR (300 MHz, DMSO-d6) δ 8.66 (s, 1H), 8.46-8.28 (m, 2H), 8.03-7.86 (m, 2H), 7.73 (t, J=8.1 Hz, 1H), 7.38-7.09 (m, 5H), 6.82 (d, J=7.2 Hz, 1H), 4.16 (dd, J=13.7, 6.8 Hz, 1H), 3.20-2.98 (m, 1H), 2.44 (dd, J=12.9, 6.6 Hz, 1H), 2.19-1.93 (m, 2H), 1.86-1.59 (m, 2H), 1.59-1.39 (m, 1H). MS (DCI/NH3) m/z 366 [M+H]+.

Workup

  1. waitcontinued for 15 minutes
  2. filtrationThe solid was collected by filtration
  3. washwashed with water
  4. dry with materialether, and dried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-9fd4a5055a7748118bb640f466f492b7
Source dataset
uspto-grants-2014_08
Patent number
US08802711B2

Reaction notes

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