Dimethylcarbamoyl Chloride → Trifluoroacetic acid

HRID 713322Notes

Reaction equation

HRID 713322 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:34]=[C:33]4[CH2:35][NH:36][CH2:37][CH2:38][C:32]4=[N:31][C:30]=3[NH:39][CH:40]([CH3:42])[CH3:41])[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:34]=[C:33]3[CH2:35][N:36]([C:3]([N:2]([CH3:6])[CH3:1])=[O:4])[CH2:37][CH2:38][C:32]3=[N:31][C:30]=2[NH:39][CH:40]([CH3:41])[CH3:42])[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 131734037HCID 131734037, compound

Product 2

HCID 6422Trifluoroacetic acidYield 175.4%HCID 118159180HCID 118159180, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dimethylcarbamic chloride (3.8 mg, 0.036 mmol) was added to a solution of (5-chloro-2-fluorophenyl)(1-(2-(isopropylamino)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-yl)piperidin-4-yl)methanone TFA salt (9.7 mg, 0.018 mmol) and triethylamine (7 μL, 0.053 mmol) in DCM (180 μL) at rt. After 1 h, the mixture was purified by HPLC Method A to give the title compound as a TFA salt (3.6 mg, 32.8%) as a yellow film. 1H NMR (400 MHz, methanol-d4) δ ppm 1.31-1.34 (m, 6H), 1.89-2.06 (m, 4H), 2.85-2.89 (m, 2H), 2.90-2.92 (m, 6H), 2.93-3.02 (m, 2H), 3.35-3.41 (m, 1H), 3.50-3.58 (m, 4H), 4.08-4.16 (m, 1H), 4.27 (s, 2H), 7.29 (dd, J=10.6, 8.8 Hz, 1H), 7.61 (ddd, J=8.8, 4.0, 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-4b99864ecabc4ea2ac565eb92274c198
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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