Trifluoroacetic acid → ((2S,4S)-4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)pyrrolidin-2-yl)methanol

HRID 1177539Notes

Reaction equation

HRID 1177539 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:26]2[CH2:30][N:29](C(OC(C)(C)C)=O)[C@H:28]([CH2:38][OH:39])[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>[F:1][C:2]1[CH:3]=[C:4]([C@H:26]2[CH2:30][NH:29][C@H:28]([CH2:38][OH:39])[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

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67111989(2S,4S)-tert-butyl 4-(3-fluoro-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)phenyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 44599523((2S,4S)-4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)pyrrolidin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2S,4S)-tert-butyl 4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (0.084 g, 0.154 mmol) in 2 mL DCM was added trifluoroacetic acid (0.200 mL) After 3 d, the reaction mixture was concentrated, dissolved in DMSO, filtered, and purified by RPHPLC, gradient, 10-100% ACN/TFA in H2O/TFA. Product-containing fractions were concentrated in vacuo to give ((2S,4S)-4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)pyrrolidin-2-yl)methanol. MS (ESI) m/z: Calculated: 445.2; Observed: 445.8 (M++1).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutiondissolved in DMSO
  3. filtrationfiltered
  4. custompurified by RPHPLC, gradient, 10-100% ACN/TFA in H2O/TFA
  5. concentrationProduct-containing fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-db4e5e03f2584f5e822d21ecaeef1bd4
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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