Trifluoroacetic acid → HCID 56597183, compound

HRID 1524257Notes

Reaction equation

HRID 1524257 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:39]=[CH:40][C:41]=1[O:42][CH3:43])[C:6]([NH:8][C@@H:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17](=[O:38])[NH:18][C:19]2[S:20][C:21]3[CH2:27][C@@H:26]([N:28]([CH2:35][CH2:36][CH3:37])C(=O)C(F)(F)F)[CH2:25][CH2:24][C:22]=3[N:23]=2)[CH:12]=1)[CH3:10])=[O:7].C([O-])([O-])=O.[K+].[K+].FC(F)(F)C(O)=O>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:39]=[CH:40][C:41]=1[O:42][CH3:43])[C:6]([NH:8][C@@H:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17](=[O:38])[NH:18][C:19]2[S:20][C:21]3[CH2:27][C@@H:26]([NH:28][CH2:35][CH2:36][CH3:37])[CH2:25][CH2:24][C:22]=3[N:23]=2)[CH:12]=1)[CH3:10])=[O:7]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 86667840HCID 86667840, compound

Product 1

HCID 56597183HCID 56597183, compoundYield 66.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

Dissolve 3,4-dimethoxy-N—[(R)-1-(3-{(S)-6-[propyl-(2,2,2-trifluoro-acetyl)-amino]-4,5,6,7-tetrahydro-benzothiazol-2-ylcarbamoyl}-phenyl)-ethyl]-benzamide (109 mg, 0.18 mmol) into 10 mL of MeOH and add 5 mL of H2O. To this add K2CO3 (200 mg, 1.50 mmol) and heat the mixture overnight at 55° C. LC-MS analysis indicates the desired material. Add trifluoroacetic acid, dissolve into MeOH and purify via the Gilson Prep HPLC system (5%-70% CH3CN/H2O) to give 62.6 mg of the title compound. MS, electrospray 523.67 (M+H), rt 1.14 min.

Workup

  1. custompurify via the Gilson Prep HPLC system (5%-70% CH3CN/H2O)

Sources & evidence

ORD record
ord-a2e97ad02727442aa5088b332f6777c8
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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