Trifluoroacetic acid → HCID 59174859, compound

HRID 1177631Notes

Reaction equation

HRID 1177631 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:26]2([N:29](C)[C:30](=O)OC(C)(C)C)[CH2:28][CH2:27]2)[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:26]2([NH:29][CH3:30])[CH2:28][CH2:27]2)[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:18][CH2:19]1)[N:11]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67111798HCID 67111798, compound

Product 1

HCID 59174859HCID 59174859, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of tert-butyl 1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)cyclopropyl(methyl)carbamate (0.03 g, 0.058 mmol) in chloroform (0.5 mL) was added trifluoroacetic acid (0.5 mL, 6.5 mmol) and stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo, and the resulting crude product was purified via reverse phase preparative HPLC to afford ′1-(3-fluoro-4-(5-(1-phenyl-cyclopropyl)[1,3]thiazolo[5,4-b]pyridin-2-yl)phenyl)-N-methylcyclopropanamine as a white amorphous solid. MS (ESI) m/z: Calculated: 415.5; Observed: 416.1 (M++1).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulting crude product was purified via reverse phase preparative HPLC

Sources & evidence

ORD record
ord-c8872f3f07854a6f85bd60fae8ea4ed8
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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