Dichloromethane → N-{3-[2-(3-Acetylamino-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-2,2-dimethyl-propionamide

HRID 1262136Notes

Reaction equation

HRID 1262136 reaction equation
[CH3:1][C:2]([CH3:24])([CH3:23])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[N:20]3[C:15]([CH:16]=[N:17][C:18](SC)=[N:19]3)=[CH:14][CH:13]=2)[CH:7]=1)=[O:4].CSC1N=CC2=CC=C([C:36]3[CH:37]=[C:38]([NH2:42])[CH:39]=[CH:40][CH:41]=3)N2N=1.C(Cl)Cl.[CH2:46]([N:48](CC)CC)[CH3:47].CC(C)(C)C(Cl)=[O:56]>>[C:46]([NH:48][C:36]1[CH:37]=[C:38]([NH:42][C:18]2[N:17]=[CH:16][C:15]3=[CH:14][CH:13]=[C:12]([C:8]4[CH:7]=[C:6]([NH:5][C:3](=[O:4])[C:2]([CH3:24])([CH3:23])[CH3:1])[CH:11]=[CH:10][CH:9]=4)[N:20]3[N:19]=2)[CH:39]=[CH:40][CH:41]=1)(=[O:56])[CH3:47]

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 667116972,2-Dimethyl-N-[3-(2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-propionamideHCID 667126823-(2-Methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenylamine

Product 1

HCID 66712052N-{3-[2-(3-Acetylamino-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-2,2-dimethyl-propionamide

Conditions

Temperature
0 °C

Procedure

2,2-Dimethyl-N-[3-(2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-propionamide. 3-(2-Methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenylamine (0.200 g, 0.780 mmol) was dissolved in Methylene chloride (10.0 mL, 156 mmol) and cooled to 0° C. Triethylamine (0.130 mL, 0.936 mmol) was added followed by 2,2-Dimethylpropanoyl chloride (0.106 mL, 0.858 mmol). The reaction mixture was allowed to warm to rt. LCMS after 30 min indicated mass of title compound. Reaction mixture was washed with water, dried over MgSO4, filtered, and concentrated. HPLC rt=3.436, purity=90%, LCMS=341.2 (M+H).

Workup

  1. temperatureto warm to rt

Sources & evidence

ORD record
ord-8331ea240a1343d298aa48c4930429c6
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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