Acryloyl chloride → Hydrochloric Acid

HRID 1050512Notes

Reaction equation

HRID 1050512 reaction equation
[N:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[N:17]=[C:18]([NH:25][C@@H:26]4[CH2:30][CH2:29][NH:28][CH2:27]4)[N:19]=[N:20][C:21]=3[C:22]([NH2:24])=[O:23])=[CH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[C:40]([Cl:44])(=[O:43])[CH:41]=[CH2:42]>CN1C(=O)CCC1>[C:40]([N:28]1[CH2:29][CH2:30][C@@H:26]([NH:25][C:18]2[N:19]=[N:20][C:21]([C:22]([NH2:24])=[O:23])=[C:16]([NH:15][C:12]3[CH:13]=[CH:14][C:9]([C:7]([N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)=[O:8])=[CH:10][CH:11]=3)[N:17]=2)[CH2:27]1)(=[O:43])[CH:41]=[CH2:42].[ClH:44]

Participants

6

Reactant 3

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 118114933HCID 118114933, compound

Product 2

HCID 313Hydrochloric AcidHCID 118114900HCID 118114900, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of (R)-5-(4-(morpholine-4-carbonyl)phenylamino)-3-(pyrrolidin-3-ylamino)-1,2,4-triazine-6-carboxamide (83) HCl salt (60 mg, 0.13 mmol) in NMP (4 mL) was added DIEA (160 μL, 0.90 mmol) and then acryloyl chloride (25 μL, 0.30 mmol). The mixture was stirred at RT for 30 min, quenched with TFA (0.2 mL), diluted with 2 mL water, and subjected to reverse phase preparative HPLC to afford the title compound (84) as an HCl salt. MS found for C22H26N8O4 as (M+H)+ 467.1, (M−H)− 465.2. UV: λ=242 nm.

Workup

  1. customquenched with TFA (0.2 mL)
  2. additiondiluted with 2 mL water

Sources & evidence

ORD record
ord-1d81de6b0614449ba78b29128186a9d8
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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