Hydrochloric Acid → HCID 86599483, compound

HRID 855049Notes

Reaction equation

HRID 855049 reaction equation
C(OC([NH:8][C:9]1[CH:33]=[CH:32][C:12]([CH2:13][C:14]2[CH:23]=[C:22]3[C:17]([CH:18]=[C:19]([C:28]([OH:30])=[O:29])[CH:20]([C:24]([F:27])([F:26])[F:25])[O:21]3)=[CH:16][C:15]=2[Cl:31])=[CH:11][CH:10]=1)=O)(C)(C)C.Cl.[O:35]1CCOCC1>O.CO>[F:25][C:24]([F:27])([F:26])[C:20]([OH:35])=[O:21].[NH2:8][C:9]1[CH:33]=[CH:32][C:12]([CH2:13][C:14]2[CH:23]=[C:22]3[C:17]([CH:18]=[C:19]([C:28]([OH:30])=[O:29])[CH:20]([C:24]([F:27])([F:25])[F:26])[O:21]3)=[CH:16][C:15]=2[Cl:31])=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid4×HCID 312751,4-Dioxane2×HCID 58934930HCID 58934930, compound

Product 1

HCID 86599483HCID 86599483, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

The 7-{4-[(tert-butoxycarbonyl)amino]benzyl}-6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid (300 mg, 0.62 mmole) was stirred in 3 mL dioxane and 0.62 mL HCl (4M) in dioxane for 6 hrs. 1HNMR indicated that the reaction mixture was 1:1 ratio of starting material:product. Additional 0.3 mL 12 N HCl in 2 mL water was added to above mixture. After the mixture was stirred for overnight, 0.3 mL 12 N HCl was added. After another overnight stirring, the solution of 3 mL 12 N HCl in 3 mL MeOH and 3 mL water was added to above mixture and the mixture was stirred for 6 hrs. The mixture was purified by RPHPLC elute with 20 to 65% ACN in water with 0.1% TFA to give the desired product as a white solid with >95% purity: ESHRMS m/z 384.0594 (M+H, C18H14O3F3ClN, Calc'd 384.0609). 1H NMR (acetone-d6/400 MHz) 7.87 (s, 1H), 7.58(s, 1H), 7.39 (d, 1H, J=8.4 Hz), 7.22 (d, 1H, J=8.4 Hz), 6.02 (s, 1H), 5.82 (q, 1H, J=7.2 Hz), 4.15 (m, 2H).

Workup

  1. stirringAfter another overnight stirring
  2. stirringthe mixture was stirred for 6 hrs
  3. customThe mixture was purified by RPHPLC
  4. washelute with 20 to 65% ACN in water with 0.1% TFA

Sources & evidence

ORD record
ord-e76e93bc67a44553b96dc142cbe36a16
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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