Dimethylcarbamoyl Chloride → Trifluoroacetic acid

HRID 713330Notes

Reaction equation

HRID 713330 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].[OH:7][C:8]([C:10]([F:13])([F:12])[F:11])=[O:9].[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([F:43])=[C:19]([C:21]([CH:23]2[CH2:28][CH2:27][N:26]([C:29]3[N:30]=[C:31]4[CH2:42][CH2:41][NH:40][CH2:39][C:32]4=[N:33][C:34]=3[NH:35][CH:36]([CH3:38])[CH3:37])[CH2:25][CH2:24]2)=[O:22])[CH:20]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([F:43])=[C:19]([CH:20]=1)[C:21]([CH:23]1[CH2:28][CH2:27][N:26]([C:29]2[N:30]=[C:31]3[CH2:42][CH2:41][N:40]([C:3]([N:2]([CH3:6])[CH3:1])=[O:4])[CH2:39][C:32]3=[N:33][C:34]=2[NH:35][CH:36]([CH3:38])[CH3:37])[CH2:25][CH2:24]1)=[O:22].[C:8]([OH:9])([C:10]([F:13])([F:12])[F:11])=[O:7]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 131734038HCID 131734038, compound

Product 2

HCID 6422Trifluoroacetic acidYield 228%HCID 118159213HCID 118159213, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dimethylcarbamic chloride (3.2 mg, 0.029 mmol) was added to a solution of (5-chloro-2-fluorophenyl)(1-(3-(isopropylamino)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-yl)piperidin-4-yl)methanone TFA salt (8.0 mg, 0.015 mmol) and triethylamine (6 μL, 0.044 mmol) in DCM (150 μL) at rt. After 1 h, the mixture was purified by HPLC Method A to give the title compound as a TFA salt (3.9 mg, 43.1%) as a yellow solid. 1H NMR (400 MHz, methanol-d4) δ ppm 1.31 (d, J=6.6 Hz, 6H), 1.85-2.05 (m, 4H), 2.77-2.84 (m, 2H), 2.91 (s, 6H), 2.93-3.01 (m, 2H), 3.36-3.41 (m, 1H), 3.51-3.59 (m, 4H), 4.07-4.15 (m, 1H), 4.31 (s, 2H), 7.28 (dd, J=10.4, 8.8 Hz, 1H), 7.61 (ddd, J=8.8, 4.3, 2.8 Hz, 1H), 7.76 (dd, J=6.1, 2.8 Hz, 1H); ESI-MS m/z [M+H]+ 504.4.

Workup

  1. customthe mixture was purified by HPLC Method A

Sources & evidence

ORD record
ord-6e2d2d6d23a8470cb0cae07fedc40739
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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