HCID 70983925, compound → HCID 136338076, compound

HRID 338981Notes

Reaction equation

HRID 338981 reaction equation
[ClH:1].C1(C[O:6][C:7]2[CH:16]=[C:15]3[C:10]([CH:11]=[CH:12][C:13]([C:17]4[N:21]5[CH:22]=[C:23]([C@@H:26]([N:31]6[CH2:35][CH2:34][C@H:33]([NH2:36])[CH2:32]6)[C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:25][C:20]5=[N:19][N:18]=4)=[N:14]3)=[CH:9][C:8]=2[F:37])CC1>Cl.CC(O)C>[ClH:1].[NH2:36][C@H:33]1[CH2:34][CH2:35][N:31]([C@H:26]([C:23]2[CH:24]=[CH:25][C:20]3[N:21]([C:17]([C:13]4[CH:12]=[CH:11][C:10]5[C:15](=[CH:16][C:7]([OH:6])=[C:8]([F:37])[CH:9]=5)[N:14]=4)=[N:18][N:19]=3)[CH:22]=2)[C:27]([F:29])([F:28])[F:30])[CH2:32]1

Participants

4

Reactant 1

HCID 70983925HCID 70983925, compound

Product 1

HCID 136338076HCID 136338076, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolvent

Procedure

(S)-1-((R)-1-(3-(7-(cyclopropylmethoxy)-6-fluoroquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-amine hydrochloride (Example 134; 50 mg, 0.1 mmol) was heated to 60° C. in 6N HCl in IPA for 3 days. After concentration, the residue was dissolve in 1 mL of MeOH then added to 2N HCl in ether. The resulting solid was dried under high vacuum to yield 2-(6-((R)-1-((S)-3-aminopyrrolidin-1-yl)-2,2,2-trifluoroethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-fluoro quinolin-7-ol hydrochloride (39 mg, 87% yield) as a solid. LCMS APCI (+) m/z 447 (M+H).

Workup

  1. concentrationAfter concentration
  2. dissolutionthe residue was dissolve in 1 mL of MeOH
  3. additionthen added to 2N HCl in ether
  4. customThe resulting solid was dried under high vacuum

Sources & evidence

ORD record
ord-d155805b021249a5b359b584b323fb25
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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