Trifluoroacetic acid → HCID 18929594, compound

HRID 1599071Notes

Reaction equation

HRID 1599071 reaction equation
C([O:5][C:6](=[O:52])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([NH:16][CH:17]2[C:23](=[O:24])[N:22]([C:25]([CH:37]([CH3:39])[CH3:38])([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[C:26](=[O:28])[NH2:27])[C:21]3[CH:40]=[CH:41][C:42]([F:44])=[CH:43][C:20]=3[N:19]([C:45]3[CH:46]=[N:47][CH:48]=[CH:49][CH:50]=3)[C:18]2=[O:51])=[O:15])[CH:8]=1)(C)(C)C.FC(F)(F)C(O)=O>>[F:44][C:42]1[CH:41]=[CH:40][C:21]2[N:22]([C:25]([CH:37]([CH3:38])[CH3:39])([C:29]3[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=3)[C:26](=[O:28])[NH2:27])[C:23](=[O:24])[CH:17]([NH:16][C:14](=[O:15])[NH:13][C:9]3[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=3)[C:6]([OH:52])=[O:5])[C:18](=[O:51])[N:19]([C:45]3[CH:46]=[N:47][CH:48]=[CH:49][CH:50]=3)[C:20]=2[CH:43]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86752411HCID 86752411, compound

Product 1

HCID 18929594HCID 18929594, compoundYield 110%

Procedure

A mixture of 84 mg of 3-(3-{7-fluoro-1-[isopropyl-(4-methoxy-phenyl)-carbamoylmethyl]-2,4-dioxo-5-pyridin-3-yl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl}-ureido)-benzoic acid tert butyl ester (0.118 mmol) and 4 mL of trifluoroacetic acid was stirred under nitrogen for 1.5 hrs. The trifluoroacetic acid was removed in vacuo and the residue was triturated with diethyl ether. The slurry was filtered, washed with diethyl ether and dried under high vacuum to provide 85 mg the title compound as a white crystalline trifluoroacetic acid salt. 1H NMR (300 MHz, d6-DMSO) d 9.33 (s, 1H), 8.70 (b, 1H), 8.57 (d, 1H, J=4.7), 8.00 (m, 1H), 7.97 (d, 1H, J=8.6), 7.61 (dd, 1H, J=5.5, 9.1), 7.55 (dd, 1H, J=4.88, 8.2), 7.47 (m, 2H), 7.26 (m, 4H), 7.05 (d, 2H, J=9.0), 6.92 (d, 1H, J=7.8) 6.82 (dd, 1H, J=2.8, 9.6), 5.10 (d, 1H, J=7.6), 4.72 (m, 1H), 4.51 (d, 1H, J=16.8), 4.14 (d, 1H, J=16.8), 3.78 (s, 3H), 0.92 (m, 6H); low resolution MS (FAB)m/e 655 (MH+).

Workup

  1. customThe trifluoroacetic acid was removed in vacuo
  2. customthe residue was triturated with diethyl ether
  3. filtrationThe slurry was filtered
  4. washwashed with diethyl ether
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-df760d9ad6494bcdacdc10e9272ce880
Source dataset
uspto-grants-1998_04
Patent number
US05739129

Reaction notes

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