Trifluoroacetic acid → HCID 9930011, compound

HRID 2113476Notes

Reaction equation

HRID 2113476 reaction equation
COC1C=C(C=CC=1C[N:25]([C:36]1[CH:37]=[C:38]2[C:43](=[CH:44][CH:45]=1)[C:42]([CH2:46][C:47]1[CH:48]=[N:49][CH:50]=[CH:51][CH:52]=1)=[N:41][NH:40][C:39]2=[O:53])[C:26]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=1)=[O:27])OCCCC(NCC1C=CC(C)=CC=1)=O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:53]=[C:39]1[C:38]2[C:43](=[CH:44][CH:45]=[C:36]([NH:25][C:26]([NH:28][C:29]3[CH:30]=[CH:31][C:32]([CH3:35])=[CH:33][CH:34]=3)=[O:27])[CH:37]=2)[C:42]([CH2:46][C:47]2[CH:48]=[N:49][CH:50]=[CH:51][CH:52]=2)=[N:41][NH:40]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69151566HCID 69151566, compound

Product 1

HCID 9930011HCID 9930011, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-{3-Methoxy-4-[1-(4-oxo-1-pyridin-3-ylmethyl-3,4-dihydro-phthalazin-6-yl)-3-p-tolyl-ureidomethyl]-phenoxy}-N-(4-methyl-benzyl)-butyramide of example 8 was suspended in a solution of 20% TFA in DCM (3 ml), and stirred at room temperature for 2 hours. The resin was filtered and the solution collected and dried up yielding 11 mg of title compound. [M+1]+=386; HPLC r.t. 4.72; 1H-NMR (DMSO-d6), diagnostic signals (ppm): 2.23 (s, 3H), 4.26 (s, 2H), 7.10 (d, 2H), 7.29 (m, 1H) 7.33 (d, 2H), 7.64 (m, 1H), 7.83 (dd, 1H), 7.89 (d, 1H), 8.40 (m, 2H), 8.56 (d, 1H), 8.70 (br. S, 1H), 9.22 (br. s, 1H), 12.38 (br. s, 1H).

Workup

  1. filtrationThe resin was filtered
  2. customthe solution collected
  3. customdried up

Sources & evidence

ORD record
ord-574da7983ddc437f99b8cb4a4781dd6b
Source dataset
uspto-grants-2008_10
Patent number
US07432263B2

Reaction notes

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