Trifluoroacetic acid → HCID 68532967, compound

HRID 644194Notes

Reaction equation

HRID 644194 reaction equation
C(OC([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:37]=[C:36]([N:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)[CH:35]=[CH:34][C:13]=1[C:14]([NH:16][C:17]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:18]=1[C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][N:23]=1)=[O:20])=[O:15])=O)(C)(C)C.C1(OC)C=CC=CC=1.[F:52][C:53]([F:58])([F:57])[C:54]([OH:56])=[O:55]>C(Cl)Cl>[F:52][C:53]([F:58])([F:57])[C:54]([OH:56])=[O:55].[NH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:37]=[C:36]([N:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)[CH:35]=[CH:34][C:13]=1[C:14]([NH:16][C:17]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:18]=1[C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][N:23]=1)=[O:20])=[O:15]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 57860831HCID 57860831, compound

Product 1

HCID 68532967HCID 68532967, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 2-[2-(2-tert-butoxycarbonylaminoethoxy)-4-(morpholin-4-yl)benzoylamino]-N-(5-chloropyridin-2-yl)-4-fluorobenzamide (570 mg, 0.93 mmol) was mixed with CH2Cl2 (5 mL), anisole (1 mL), and trifluoroacetic acid (2 mL). The mixture was stirred at ambient temperature for 2 hours, concentrated to dryness, mixed with diethyl ether, and sonicated for 5 minutes to give a white fluffy solid which was filtered to give 490 mg (62%) of the desired product as the trifluoroacetate salt.

Workup

  1. concentrationconcentrated to dryness
  2. additionmixed with diethyl ether
  3. customsonicated for 5 minutes
  4. customto give a white fluffy solid which
  5. filtrationwas filtered

Sources & evidence

ORD record
ord-25e9f664d7494a27b8f3493ed81b7beb
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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