Trifluoroacetic acid methylene chloride → Trifluoroacetic acid

HRID 2365452Notes

Reaction equation

HRID 2365452 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:48]=[CH:47][C:9]([CH2:10][NH:11][C:12]2[N:17]=[C:16]([NH:18][C:19]3[CH:40]=[CH:39][C:22]([C:23]([NH:25][CH2:26][C:27]([CH3:38])([CH3:37])[CH2:28][NH:29]C(=O)OC(C)(C)C)=[O:24])=[CH:21][CH:20]=3)[CH:15]=[C:14]([O:41][CH2:42][C:43]([F:46])([F:45])[F:44])[N:13]=2)=[CH:8][CH:7]=1.[C:49]([OH:55])([C:51]([F:54])([F:53])[F:52])=[O:50].C(Cl)Cl>>[C:49]([OH:55])([C:51]([F:54])([F:53])[F:52])=[O:50].[NH2:29][CH2:28][C:27]([CH3:38])([CH3:37])[CH2:26][NH:25][C:23](=[O:24])[C:22]1[CH:21]=[CH:20][C:19]([NH:18][C:16]2[CH:15]=[C:14]([O:41][CH2:42][C:43]([F:44])([F:46])[F:45])[N:13]=[C:12]([NH:11][CH2:10][C:9]3[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH2:3][CH2:2][Br:1])=[CH:48][CH:47]=3)[N:17]=2)=[CH:40][CH:39]=1

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86680944HCID 86680944, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 86680943HCID 86680943, compound

Procedure

tert-butyl (3-(4-((2-((4-(3-bromopropoxy)benzyl)amino)-6-(2,2,2-trifluoroethoxy)pyrimidin-4-yl)amino)benzamido)-2,2-dimethylpropyl)carbamate (35 mg, 0.047 mmol) was stirred in TFA/DCM (1:1) solution (2 mL) for 1 h. The solution was concentrated and free TFA to give N-(3-amino-2,2-dimethylpropyl)-4-((2-((4-(3-bromopropoxy)benzyl)amino)-6-(2,2,2-trifluoroethoxy)pyrimidin-4-yl)amino)benzamide which was carried to the next step without purification.

Workup

  1. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-96a3b5542e594a4fb3307670b52febce
Source dataset
uspto-grants-2014_04
Patent number
US08697706B2

Reaction notes

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