Trifluoroacetic acid → HCID 24965796, compound

HRID 1161865Notes

Reaction equation

HRID 1161865 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[N:21]=[C:20]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=2)[N:19]([CH2:32][C:33](=[O:39])[NH:34][C:35]([CH3:38])([CH3:37])[CH3:36])[C:18]3=[O:40])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl.FC(F)(F)C(O)=O>>[C:35]([NH:34][C:33](=[O:39])[CH2:32][N:19]1[C:18](=[O:40])[C:17]2[C:22](=[CH:23][CH:24]=[C:15]([N:11]3[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]3)[CH:16]=2)[N:21]=[C:20]1[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=1)([CH3:38])([CH3:36])[CH3:37]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21863450Trifluoroacetic acid methylene chlorideHCID 59519096HCID 59519096, compound

Product 1

HCID 24965796HCID 24965796, compoundYield 68%

Procedure

4-[3-(tert-Butylcarbamoylmethyl)-2-(3-chlorophenyl)-4-oxo-3,4-dihydroquinazolin-6-yl]perhydro-1,4-diazepine-1-carboxylic acid tert-butyl ester (INTERMEDIATE VIII.1) (38.9 mg, 0.068 mmol) was treated with TFA:DCM (1:1 (v/v), 1 mL) and the solution stirred at room temperature for 40 min. The volatiles were removed in vacuo and the residue partitioned between DCM and 1 M NaOH (aq.). The organics were dried (Na2SO4) and concentrated in vacuo to yield N-tert-butyl-2-[2-(3-chlorophenyl)-4-oxo-6-perhydro-1,4-diazepin-1-yl-4H-quinazolin-3-yl]acetamide (EXAMPLE 1a) (27 mg, 0.046 mmol, 68%) as the trifluoroacetic acid salt.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue partitioned between DCM and 1 M NaOH (aq.)
  3. dry with materialThe organics were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9d10390594104ace8842eb30fe7e8043
Source dataset
uspto-grants-2010_10
Patent number
US07820649B2

Reaction notes

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