Trifluoroacetic acid → HCID 86753037, compound

HRID 482351Notes

Reaction equation

HRID 482351 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[NH:24][C:25](=[O:53])[NH:26][CH:27]2[C:33](=[O:34])[N:32]([CH2:35][C:36]([N:38]([CH:45]([CH3:47])[CH3:46])[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[O:37])[C:31]3[CH:48]=[CH:49][CH:50]=[CH:51][C:30]=3[C:29]([CH3:52])=[N:28]2)[CH:17]=[N:16]1)=O)(C)(C)C>>[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[NH:24][C:25](=[O:53])[NH:26][CH:27]2[C:33](=[O:34])[N:32]([CH2:35][C:36]([N:38]([CH:45]([CH3:47])[CH3:46])[C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[O:37])[C:31]3[CH:48]=[CH:49][CH:50]=[CH:51][C:30]=3[C:29]([CH3:52])=[N:28]2)[CH:17]=[N:16]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19063663HCID 19063663, compound

Product 1

HCID 86753037HCID 86753037, compoundYield 97.5%

Procedure

Trifluoroacetic acid (2.0 mL) and 2-(3-{3-[1-(tert-Butoxycarbonyl)-indazol-7-yl]-ureido}-5-methyl-2-oxo-2,3-dihydro-benzo[e][1,4]diazepin-1yl)-N-isopropyl-N-phenyl-acetamide (75 mg, 0.120 mmol), prepared as in Example 4A, are combined, cooled to 0-5--C. with an ice water bath, and stirred under nitrogen for 15 min. The reaction mixture is concentrated in vacuo to an oil, triturated with a mixture of diethyl ether and n-hexane and then concentrated again. This process is repeated several times until a solid is obtained on concentration. The product is dried under high vacuum overnight at room temperature and then at 65--C. overnight to give the title compound as a crystalline solid (61 mg, 0.117 mmol). The pure material is then lyophilized from acetonitrile/water. 1H NMR (300 MHz, CDCl3) δ=1.08-1.12 (m, 6H); 2.73 (s, 3H); 4.11 (d, J=16.8 Hz,1H); 4.24 (d, J=16.6 Hz, 1H); 4.93-5.08 (m, 1H); 5.76 (b, 1H); 6.99-7.75 (m, 14H); 8.00 (b, 1H); 8.83 (b, 1H). MS(FAB): [M+H]+ =524.

Workup

  1. temperaturecooled to 0-5
  2. concentrationThe reaction mixture is concentrated in vacuo to an oil
  3. customtriturated with a mixture of diethyl ether and n-hexane
  4. concentrationconcentrated again
  5. customis obtained on concentration
  6. customThe product is dried under high vacuum overnight at room temperature

Sources & evidence

ORD record
ord-15070332bcb34349866523078fd0672a
Source dataset
uspto-grants-1998_08
Patent number
US05795887

Reaction notes

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