Dimethylcarbamoyl Chloride → Hydrochloric Acid

HRID 1050526Notes

Reaction equation

HRID 1050526 reaction equation
[CH3:1][O:2][C:3]1[CH:39]=[CH:38][C:6]([C:7]([NH:9][C@@H:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]3[N:17]=[C:18]([NH:25][C:26]4[CH:31]=[CH:30][C:29]([CH:32]5[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]5)=[CH:28][CH:27]=4)[C:19]([C:22]([NH2:24])=[O:23])=[N:20][CH:21]=3)[CH2:11]2)=[O:8])=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[CH3:49][N:50]([CH3:54])[C:51]([Cl:53])=[O:52]>CN1C(=O)CCC1>[CH3:49][N:50]([CH3:54])[C:51]([N:35]1[CH2:36][CH2:37][CH:32]([C:29]2[CH:30]=[CH:31][C:26]([NH:25][C:18]3[C:19]([C:22]([NH2:24])=[O:23])=[N:20][CH:21]=[C:16]([N:12]4[CH2:13][CH2:14][CH2:15][C@@H:10]([NH:9][C:7](=[O:8])[C:6]5[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:39][CH:38]=5)[CH2:11]4)[N:17]=3)=[CH:27][CH:28]=2)[CH2:33][CH2:34]1)=[O:52].[ClH:53]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 81531DiisopropylethylamineHCID 118133410HCID 118133410, compound

Product 2

HCID 313Hydrochloric AcidYield 509.4%HCID 118115277HCID 118115277, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Compound 163 (40 mg, 0.07 mmol) was dissolved in 3 mL NMP. To it were added DIEA (125 μL, 0.71 mmol) and then dimethylcarbamic chloride (20 μL, 0.21 mmol). The reaction was quenched in 1 h using TFA (0.2 mL). The mixture was directly subjected to reverse phase preparative HPLC to isolate (R)-3-(4-(1-(dimethylcarbamoyl)piperidin-4-yl)phenylamino)-5-(3-(4-methoxybenzamido)piperidin-1-yl)pyrazine-2-carboxamide (172) as HCl salt (13 mg). MS found for C32H40N8O4 as (M+H)+ 601.3, (M−H)− 599.3. UV: λ=257, 279, 304, 336, 372 nm.

Workup

  1. customThe reaction was quenched in 1 h

Sources & evidence

ORD record
ord-3a3c5d3082bf468599f3d467bd42885f
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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