Dimethylcarbamoyl Chloride → Trifluoroacetic acid

HRID 713333Notes

Reaction equation

HRID 713333 reaction equation
[OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].[CH:8]1([NH:12][C:13]2[N:14]=[C:15]3[CH2:38][CH2:37][NH:36][CH2:35][C:16]3=[N:17][C:18]=2[N:19]2[CH2:24][CH2:23][CH:22]([O:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=3[F:34])[CH2:21][CH2:20]2)[CH2:11][CH2:10][CH2:9]1.[CH3:39][N:40]([CH3:44])[C:41](Cl)=[O:42].C(N(CC)CC)C>C(Cl)Cl>[CH:8]1([NH:12][C:13]2[N:14]=[C:15]3[CH2:38][CH2:37][N:36]([C:41]([N:40]([CH3:44])[CH3:39])=[O:42])[CH2:35][C:16]3=[N:17][C:18]=2[N:19]2[CH2:20][CH2:21][CH:22]([O:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=3[F:34])[CH2:23][CH2:24]2)[CH2:11][CH2:10][CH2:9]1.[C:2]([OH:3])([C:4]([F:7])([F:6])[F:5])=[O:1]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 131734040HCID 131734040, compound

Product 2

HCID 6422Trifluoroacetic acidYield 311.3%HCID 118159378HCID 118159378, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-cyclobutyl-3-(4-(2-fluoro-4-methoxyphenoxy)piperidin-1-yl)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-amine TFA salt (10.6 mg, 0.020 mmol), dimethylcarbamic chloride (4.2 mg, 0.039 mmol) and triethylamine (5.9 mg, 0.059 mmol) in DCM (200 μL) was stirred at room temperature for 30 min. The mixture was purified by HPLC Method A to give the title compound as a TFA salt (7.1 mg, 59.2%) as a yellow film. 1H NMR (400 MHz, methanol-d4) δ ppm 1.77-1.87 (m, 2H), 1.90-2.00 (m, 2H), 2.03-2.15 (m, 4H), 2.39-2.49 (m, 2H), 2.81-2.87 (m, 2H), 2.90 (s, 6H), 2.98-3.08 (m, 2H), 3.38-3.47 (m, 2H), 3.54 (t, J=5.8 Hz, 2H), 3.76 (s, 3H), 4.26 (s, 2H), 4.33-4.47 (m, 2H), 6.67 (dd, J=9.1, 1.5 Hz, 1H), 6.74 (dd, J=12.8, 2.9 Hz, 1H), 7.08 (t, J=9.2 Hz, 1H); ESI-MS m/z [M+H]+ 499.4.

Workup

  1. customThe mixture was purified by HPLC Method A

Sources & evidence

ORD record
ord-5c5bb63aabd34e65a602aba7940f75a1
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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